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253128-10-8

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  • (2S,5S)-5-[2-[(2S,4R,6R)-6-[[(2S,3S,4R,5R)-5-[(2S)-2,3-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]tetrahydro-4-methoxy-3-[(phenylsulfonyl)methyl]-2-furanyl]methyl]tetrahydro-4-methyl-5-methylene

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  • 2-Furanpropanol, 5-[2-[(2S,4R,6R)-6-[[(2S,3S,4R,5R)-5-[(2S)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]tetrahydro-4-methoxy-3-[(phenylsulfonyl)methyl]-2-furanyl]methyl]tetrahydro-4-methyl-5-

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  • 2-Furanpropanol, 5-[2-[(2S,4R,6R)-6-[[(2S,3S,4R,5R)-5-[(2S)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]tetrahydro-4-methoxy-3-[(phenylsulfonyl)methyl]-2-furanyl]methyl]tetrahydro-4-methyl-5-

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  • 2-Furanpropanol, 5-[2-[(2S,4R,6R)-6-[[(2S,3S,4R,5R)-5-[(2S)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]tetrahydro-4-methoxy-3-[(phenylsulfonyl) methyl]-2-furanyl]methyl]tetrahydro-4-methyl-5

    Cas No: 253128-10-8

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    Cas No: 253128-10-8

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253128-10-8 Usage

General Description

The chemical "(2-Furanpropanol, 5-[2-[(2S,4R,6R)-6-[[(2S,3S,4R,5R)-5-[(2S)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]tetrahydro-4-methoxy-3-[(phenylsulfonyl)methyl]-2-furanyl]methyl]tetrahydro-4-methyl-5-methylene-2H-pyran-2-yl]ethyl]" is a complex organic compound containing furan ring and propanol functional group. It also contains multiple stereocenters, methyl and methoxy groups, and a phenylsulfonyl moiety. (2-Furanpropanol, 5-[2-[(2S,4R,6R)-6-[[(2S,3S,4R,5R)-5-[(2S)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]tetrahydro-4-methoxy-3-[(phenylsulfonyl) methyl]-2-furanyl]methyl]tetrahydro-4-methyl-5-methylene-2H-pyran-2-yl]ethyl] is a highly complex and specialized chemical and may have specific applications in the pharmaceutical, agrochemical, or material science industries.

Check Digit Verification of cas no

The CAS Registry Mumber 253128-10-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,5,3,1,2 and 8 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 253128-10:
(8*2)+(7*5)+(6*3)+(5*1)+(4*2)+(3*8)+(2*1)+(1*0)=108
108 % 10 = 8
So 253128-10-8 is a valid CAS Registry Number.

253128-10-8Synthetic route

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran -2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate
253128-09-5

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran -2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
With diisobutylaluminium hydride In dichloromethane at -78℃;97%
With methanol; diisobutylaluminium hydride In toluene at -65 - 20℃;92%
With diisobutylaluminium hydride In toluene at -70℃; Large scale;79%
C52H90O12SSi2
1316279-00-1

C52H90O12SSi2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Stage #1: C52H90O12SSi2 With pyridine; Methanesulfonic anhydride In dichloromethane at 0 - 20℃; for 1h;
Stage #2: With methanol; sodium methylate In tetrahydrofuran at 0 - 20℃; for 1h; Williamson Synthesis;
87%
thiophenol
108-98-5

thiophenol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
2: 81 percent / TPAP; NMO / acetonitrile / 20 °C
3: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(2R,3S)-3-[2-(benzyloxy)ethyl]oxiran-2-methanol
126107-76-4

(2R,3S)-3-[2-(benzyloxy)ethyl]oxiran-2-methanol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 20 steps
1.1: 93 percent / t-BuOK
2.1: n-BuLi / toluene
2.2: 69 percent / BF3*OEt / toluene / -50 °C
3.1: 99 percent / H2; quinoline / Pd/CaCO3 / hexane; CH2Cl2 / 20 °C
4.1: 99 percent / pyridine; DMAP / CH2Cl2 / 20 °C
5.1: aq. OsO4; NMO / 2-methyl-propan-2-ol / 20 °C
6.1: 58 percent / pyridine / 20 °C
7.1: Triton B / methanol / 20 °C
8.1: methylmagnesium bromide / tetrahydrofuran / 45 °C
9.1: t-BuOK / tetrahydrofuran / 0 °C
10.1: aq. HCl / tetrahydrofuran; methanol / 20 °C
11.1: imidazole / dimethylformamide / 20 °C
12.1: H2 / Raney Ni / ethanol
13.1: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
14.1: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
15.1: KHMDS / tetrahydrofuran / 0 °C
16.1: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
17.1: 98 percent / Et3N / CH2Cl2 / 0 °C
18.1: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
19.1: 81 percent / TPAP; NMO / acetonitrile / 20 °C
20.1: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane
805246-98-4

(2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: n-BuLi / toluene
1.2: 69 percent / BF3*OEt / toluene / -50 °C
2.1: 99 percent / H2; quinoline / Pd/CaCO3 / hexane; CH2Cl2 / 20 °C
3.1: 99 percent / pyridine; DMAP / CH2Cl2 / 20 °C
4.1: aq. OsO4; NMO / 2-methyl-propan-2-ol / 20 °C
5.1: 58 percent / pyridine / 20 °C
6.1: Triton B / methanol / 20 °C
7.1: methylmagnesium bromide / tetrahydrofuran / 45 °C
8.1: t-BuOK / tetrahydrofuran / 0 °C
9.1: aq. HCl / tetrahydrofuran; methanol / 20 °C
10.1: imidazole / dimethylformamide / 20 °C
11.1: H2 / Raney Ni / ethanol
12.1: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
13.1: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
14.1: KHMDS / tetrahydrofuran / 0 °C
15.1: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
16.1: 98 percent / Et3N / CH2Cl2 / 0 °C
17.1: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
18.1: 81 percent / TPAP; NMO / acetonitrile / 20 °C
19.1: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(S)-3-[(2R,3R,4S,5S)-5-(2-Benzyloxy-ethyl)-3-methoxy-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-propane-1,2-diol

(S)-3-[(2R,3R,4S,5S)-5-(2-Benzyloxy-ethyl)-3-methoxy-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-propane-1,2-diol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: imidazole / dimethylformamide / 20 °C
2: H2 / Raney Ni / ethanol
3: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
4: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
5: KHMDS / tetrahydrofuran / 0 °C
6: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
7: 98 percent / Et3N / CH2Cl2 / 0 °C
8: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
9: 81 percent / TPAP; NMO / acetonitrile / 20 °C
10: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(Z)-(3S,4S)-1-Benzyloxy-7-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxymethyl)-hept-5-en-3-ol
805247-15-8

(Z)-(3S,4S)-1-Benzyloxy-7-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxymethyl)-hept-5-en-3-ol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: 99 percent / pyridine; DMAP / CH2Cl2 / 20 °C
2: aq. OsO4; NMO / 2-methyl-propan-2-ol / 20 °C
3: 58 percent / pyridine / 20 °C
4: Triton B / methanol / 20 °C
5: methylmagnesium bromide / tetrahydrofuran / 45 °C
6: t-BuOK / tetrahydrofuran / 0 °C
7: aq. HCl / tetrahydrofuran; methanol / 20 °C
8: imidazole / dimethylformamide / 20 °C
9: H2 / Raney Ni / ethanol
10: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
11: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
12: KHMDS / tetrahydrofuran / 0 °C
13: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
14: 98 percent / Et3N / CH2Cl2 / 0 °C
15: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
16: 81 percent / TPAP; NMO / acetonitrile / 20 °C
17: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(3S,4S)-1-Benzyloxy-7-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxymethyl)-hept-5-yn-3-ol
805246-99-5

(3S,4S)-1-Benzyloxy-7-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxymethyl)-hept-5-yn-3-ol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1: 99 percent / H2; quinoline / Pd/CaCO3 / hexane; CH2Cl2 / 20 °C
2: 99 percent / pyridine; DMAP / CH2Cl2 / 20 °C
3: aq. OsO4; NMO / 2-methyl-propan-2-ol / 20 °C
4: 58 percent / pyridine / 20 °C
5: Triton B / methanol / 20 °C
6: methylmagnesium bromide / tetrahydrofuran / 45 °C
7: t-BuOK / tetrahydrofuran / 0 °C
8: aq. HCl / tetrahydrofuran; methanol / 20 °C
9: imidazole / dimethylformamide / 20 °C
10: H2 / Raney Ni / ethanol
11: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
12: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
13: KHMDS / tetrahydrofuran / 0 °C
14: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
15: 98 percent / Et3N / CH2Cl2 / 0 °C
16: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
17: 81 percent / TPAP; NMO / acetonitrile / 20 °C
18: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(2R,3R,4R,5S)-5-(2-Benzyloxy-ethyl)-2-((S)-2,2-diethyl-[1,3]dioxolan-4-ylmethyl)-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-ol

(2R,3R,4R,5S)-5-(2-Benzyloxy-ethyl)-2-((S)-2,2-diethyl-[1,3]dioxolan-4-ylmethyl)-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-ol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: t-BuOK / tetrahydrofuran / 0 °C
2: aq. HCl / tetrahydrofuran; methanol / 20 °C
3: imidazole / dimethylformamide / 20 °C
4: H2 / Raney Ni / ethanol
5: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
6: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
7: KHMDS / tetrahydrofuran / 0 °C
8: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
9: 98 percent / Et3N / CH2Cl2 / 0 °C
10: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
11: 81 percent / TPAP; NMO / acetonitrile / 20 °C
12: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(S)-4-[(2R,3R,4S,5S)-5-(2-Benzyloxy-ethyl)-3-methoxy-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-ylmethyl]-2,2-diethyl-[1,3]dioxolane
805247-02-3

(S)-4-[(2R,3R,4S,5S)-5-(2-Benzyloxy-ethyl)-3-methoxy-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-ylmethyl]-2,2-diethyl-[1,3]dioxolane

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: aq. HCl / tetrahydrofuran; methanol / 20 °C
2: imidazole / dimethylformamide / 20 °C
3: H2 / Raney Ni / ethanol
4: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
5: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
6: KHMDS / tetrahydrofuran / 0 °C
7: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
8: 98 percent / Et3N / CH2Cl2 / 0 °C
9: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
10: 81 percent / TPAP; NMO / acetonitrile / 20 °C
11: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
Acetic acid (Z)-(1S,2S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxymethyl)-pent-3-enyl ester
805247-00-1

Acetic acid (Z)-(1S,2S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxymethyl)-pent-3-enyl ester

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: aq. OsO4; NMO / 2-methyl-propan-2-ol / 20 °C
2: 58 percent / pyridine / 20 °C
3: Triton B / methanol / 20 °C
4: methylmagnesium bromide / tetrahydrofuran / 45 °C
5: t-BuOK / tetrahydrofuran / 0 °C
6: aq. HCl / tetrahydrofuran; methanol / 20 °C
7: imidazole / dimethylformamide / 20 °C
8: H2 / Raney Ni / ethanol
9: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
10: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
11: KHMDS / tetrahydrofuran / 0 °C
12: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
13: 98 percent / Et3N / CH2Cl2 / 0 °C
14: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
15: 81 percent / TPAP; NMO / acetonitrile / 20 °C
16: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetaldehyde
252905-00-3

[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-acetaldehyde

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
2: KHMDS / tetrahydrofuran / 0 °C
3: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
4: 98 percent / Et3N / CH2Cl2 / 0 °C
5: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
6: 81 percent / TPAP; NMO / acetonitrile / 20 °C
7: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
Methanesulfonic acid (2R,3R,4S,5S)-5-(2-benzyloxy-ethyl)-2-((S)-2,2-diethyl-[1,3]dioxolan-4-ylmethyl)-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

Methanesulfonic acid (2R,3R,4S,5S)-5-(2-benzyloxy-ethyl)-2-((S)-2,2-diethyl-[1,3]dioxolan-4-ylmethyl)-4-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: methylmagnesium bromide / tetrahydrofuran / 45 °C
2: t-BuOK / tetrahydrofuran / 0 °C
3: aq. HCl / tetrahydrofuran; methanol / 20 °C
4: imidazole / dimethylformamide / 20 °C
5: H2 / Raney Ni / ethanol
6: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
7: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
8: KHMDS / tetrahydrofuran / 0 °C
9: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
10: 98 percent / Et3N / CH2Cl2 / 0 °C
11: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
12: 81 percent / TPAP; NMO / acetonitrile / 20 °C
13: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
Acetic acid (1S,2R)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

Acetic acid (1S,2R)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 58 percent / pyridine / 20 °C
2: Triton B / methanol / 20 °C
3: methylmagnesium bromide / tetrahydrofuran / 45 °C
4: t-BuOK / tetrahydrofuran / 0 °C
5: aq. HCl / tetrahydrofuran; methanol / 20 °C
6: imidazole / dimethylformamide / 20 °C
7: H2 / Raney Ni / ethanol
8: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
9: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
10: KHMDS / tetrahydrofuran / 0 °C
11: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
12: 98 percent / Et3N / CH2Cl2 / 0 °C
13: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
14: 81 percent / TPAP; NMO / acetonitrile / 20 °C
15: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol
252904-99-7

2-[(2S,3S,4R,5R)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-ethanol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
2: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
3: KHMDS / tetrahydrofuran / 0 °C
4: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
5: 98 percent / Et3N / CH2Cl2 / 0 °C
6: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
7: 81 percent / TPAP; NMO / acetonitrile / 20 °C
8: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
(2S,3S,4R,5R)-2-(2-Benzyloxy-ethyl)-5-[(S)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan

(2S,3S,4R,5R)-2-(2-Benzyloxy-ethyl)-5-[(S)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxymethyl)-tetrahydro-furan

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: H2 / Raney Ni / ethanol
2: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
3: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
4: KHMDS / tetrahydrofuran / 0 °C
5: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
6: 98 percent / Et3N / CH2Cl2 / 0 °C
7: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
8: 81 percent / TPAP; NMO / acetonitrile / 20 °C
9: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester
805247-01-2

Acetic acid (1S,2S,3R,4S)-1-(2-benzyloxy-ethyl)-5-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3,4-bis-methanesulfonyloxy-2-(4-methoxy-benzyloxymethyl)-pentyl ester

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: Triton B / methanol / 20 °C
2: methylmagnesium bromide / tetrahydrofuran / 45 °C
3: t-BuOK / tetrahydrofuran / 0 °C
4: aq. HCl / tetrahydrofuran; methanol / 20 °C
5: imidazole / dimethylformamide / 20 °C
6: H2 / Raney Ni / ethanol
7: 73 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -60 - 0 °C
8: aq. NiCl2; CrCl2 / tetrahydrofuran; dimethylformamide / 20 °C
9: KHMDS / tetrahydrofuran / 0 °C
10: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
11: 98 percent / Et3N / CH2Cl2 / 0 °C
12: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
13: 81 percent / TPAP; NMO / acetonitrile / 20 °C
14: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
2,2-dimethyl-propionic acid 3-{5-[2-(6-{5-[2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-hydroxymethyl-4-methoxy-tetrahydro-furan-2-ylmethyl}-4-methyl-5-methylene-tetrahydro-pyran-2-yl)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propyl ester
253127-99-0

2,2-dimethyl-propionic acid 3-{5-[2-(6-{5-[2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-hydroxymethyl-4-methoxy-tetrahydro-furan-2-ylmethyl}-4-methyl-5-methylene-tetrahydro-pyran-2-yl)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propyl ester

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / Et3N / CH2Cl2 / 0 °C
2: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
3: 81 percent / TPAP; NMO / acetonitrile / 20 °C
4: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
C45H84O11SSi2
253128-07-3

C45H84O11SSi2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
2: 81 percent / TPAP; NMO / acetonitrile / 20 °C
3: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
C50H86O8SSi2
253128-08-4

C50H86O8SSi2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / TPAP; NMO / acetonitrile / 20 °C
2: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
Multi-step reaction with 2 steps
1: ammonium molibdate; urea hydrogen peroxide adduct / ethanol / 12 h / 0 - 20 °C
2: methanol; diisobutylaluminium hydride / toluene / -65 - 20 °C
View Scheme
C52H90O10Si2
253127-98-9

C52H90O10Si2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
2: 98 percent / Et3N / CH2Cl2 / 0 °C
3: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
4: 81 percent / TPAP; NMO / acetonitrile / 20 °C
5: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
C53H94O13SSi2

C53H94O13SSi2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: KHMDS / tetrahydrofuran / 0 °C
2: 59 percent / DDQ / CH2Cl2 / 20 °C / pH 7
3: 98 percent / Et3N / CH2Cl2 / 0 °C
4: 96 percent / i-Pr2NEt / dimethylformamide / 20 °C
5: 81 percent / TPAP; NMO / acetonitrile / 20 °C
6: 97 percent / DIBAL / CH2Cl2 / -78 °C
View Scheme
2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde

2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
1.2: 1 h / 0 - 5 °C
2.1: dmap; pyridine / 3 h / 20 - 23 °C
3.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
4.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
4.2: 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide; triethylamine; nickel dichloride; chromium dichloride / tetrahydrofuran / 25 °C / Inert atmosphere
2: potassium hexamethylsilazane / toluene; tetrahydrofuran / -20 °C
3: diisobutylaluminium hydride / toluene / -70 °C / Large scale
View Scheme
Multi-step reaction with 7 steps
1: (1S)-10-camphorsulfonic acid / 72 h / 20 °C
2: pyridine / dichloromethane / 64 h / 20 - 40 °C
3: boron trifluoride diethyl etherate / dichloromethane / 7 h / -30 - -20 °C
4: tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; formic acid; triethylamine / tetrahydrofuran / 46 h / 60 °C
5: magnesium methanolate / methanol; tetrahydrofuran / 2 h / 20 °C
6: 1H-imidazole / N,N-dimethyl-formamide / 75 h / 20 °C
7: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C
View Scheme
C27H50O6Si
1316278-85-9

C27H50O6Si

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 1 h / -30 - -25 °C
2.1: hydrogenchloride / isopropyl alcohol; methanol / 1 h / 20 °C
3.1: pyridine / dichloromethane / 1 h / -10 - 0 °C
4.1: sodium iodide / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 22 °C
5.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
5.2: 1 h / 0 - 5 °C
6.1: dmap; pyridine / 3 h / 20 - 23 °C
7.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
8.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
8.2: 1 h / 0 - 20 °C
View Scheme
C28H49F3O8SSi
1316278-90-6

C28H49F3O8SSi

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: hydrogenchloride / isopropyl alcohol; methanol / 1 h / 20 °C
2.1: pyridine / dichloromethane / 1 h / -10 - 0 °C
3.1: sodium iodide / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 22 °C
4.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
4.2: 1 h / 0 - 5 °C
5.1: dmap; pyridine / 3 h / 20 - 23 °C
6.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
7.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
7.2: 1 h / 0 - 20 °C
View Scheme
C22H35F3O8S
1316278-89-3

C22H35F3O8S

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / dichloromethane / 1 h / -10 - 0 °C
2.1: sodium iodide / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 22 °C
3.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
3.2: 1 h / 0 - 5 °C
4.1: dmap; pyridine / 3 h / 20 - 23 °C
5.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
6.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
6.2: 1 h / 0 - 20 °C
View Scheme
C23H34F6O10S2

C23H34F6O10S2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium iodide / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 22 °C
2.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
2.2: 1 h / 0 - 5 °C
3.1: dmap; pyridine / 3 h / 20 - 23 °C
4.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
5.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
5.2: 1 h / 0 - 20 °C
View Scheme
3-((2S,3aS,5R,7aS)-3a-(iodomethyl)-5-((R)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)but-3-en-1-yl)hexahydro-2H-furo[3,2-b]pyran-2-yl)propyl pivalate
1316278-93-9

3-((2S,3aS,5R,7aS)-3a-(iodomethyl)-5-((R)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)but-3-en-1-yl)hexahydro-2H-furo[3,2-b]pyran-2-yl)propyl pivalate

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
1.2: 1 h / 0 - 5 °C
2.1: dmap; pyridine / 3 h / 20 - 23 °C
3.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
4.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
4.2: 1 h / 0 - 20 °C
View Scheme
C50H87IO11SSi2
1316278-94-0

C50H87IO11SSi2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dmap; pyridine / 3 h / 20 - 23 °C
2.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
3.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
3.2: 1 h / 0 - 20 °C
View Scheme
C52H89IO12SSi2
1316278-99-5

C52H89IO12SSi2

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: zinc; acetic acid / water; tetrahydrofuran / 3 h / 0 - 20 °C
2.1: Methanesulfonic anhydride; pyridine / dichloromethane / 1 h / 0 - 20 °C
2.2: 1 h / 0 - 20 °C
View Scheme
3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

3-((2S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-al

3-((2S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-al

Conditions
ConditionsYield
With Dess-Martin periodane In dichloromethane; water at 25℃;99%
[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde
252905-91-2

[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

3-{(2S,5S)-5-[2-((2S,4R,6R)-6-{[(2S,3S,4R,5R)-3-[(1RS,2RS)-3-[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tert-butyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]-2-hydroxy-1-(phenylsulfonyl)propyl]-5-((2S)-2,3-bis{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-methoxytetrahydrofuran-2-yl]methyl}-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylenetetrahydrofuran-2-yl}propan-1-ol
253128-11-9

3-{(2S,5S)-5-[2-((2S,4R,6R)-6-{[(2S,3S,4R,5R)-3-[(1RS,2RS)-3-[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tert-butyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]-2-hydroxy-1-(phenylsulfonyl)propyl]-5-((2S)-2,3-bis{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-methoxytetrahydrofuran-2-yl]methyl}-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylenetetrahydrofuran-2-yl}propan-1-ol

Conditions
ConditionsYield
Stage #1: 3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol With n-butyllithium In tetrahydrofuran; hexane at 5℃; Industrial scale;
Stage #2: [(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde In tetrahydrofuran; hexane; n-heptane at -50℃; Reagent/catalyst; Temperature; Industrial scale;
95%
[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde
252905-91-2

[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

C77H142O15SSi5

C77H142O15SSi5

Conditions
ConditionsYield
Stage #1: 3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 0.166667h;
Stage #2: [(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde In tetrahydrofuran; hexane at -78 - -65℃; for 0.5h;
84%
[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde
252905-91-2

[(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

C76H137IO15SSi5

C76H137IO15SSi5

Conditions
ConditionsYield
Stage #1: 3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol With n-butyllithium In 1,2-dimethoxyethane
Stage #2: [(2R,4aS,6S,7R,8S,8aS)-7,8-bis{[tert-butyl(dimethyl)silyl]oxy}-6-((1S,2E)-1-{[tertbutyl(dimethyl)silyl]oxy}-3-iodoprop-2-en-1-yl)octahydropyrano[3,2-b]pyran-2-yl]acetaldehyde In 1,2-dimethoxyethane at -40 - -26℃;
C31H61IO6Si3

C31H61IO6Si3

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol
253128-10-8

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

C76H139IO15SSi5

C76H139IO15SSi5

Conditions
ConditionsYield
Stage #1: 3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol With n-butyllithium In 1,2-dimethoxyethane at -40℃; for 0.583333h;
Stage #2: C31H61IO6Si3 In 1,2-dimethoxyethane at -40℃; for 0.666667h;
52 mg

253128-10-8Relevant articles and documents

INTERMEDIATE FOR PREPARING ERIBULIN MESYLATE AND PROCESS FOR PREPARING THE SAME

-

, (2020/12/04)

The present invention relates to a process for preparing a compound of formula (6) which is an intermediate for the preparation of eribulin mesylate with high yields and high purity, and an intermediate therefor.

MACROCYCLIZATION REACTIONS AND INTERMEDIATES USEFUL IN THE SYNTHESIS OF ANALOGS OF HALICHONDRIN B

-

, (2015/05/19)

The invention provides methods for the synthesis of eribulin or a pharmaceutically acceptable salt thereof (e.g., eribulin mesylate) through a macrocyclization strategy. The macrocyclization strategy of the present invention involves subjecting a non-macrocyclic intermediate to a carbon-carbon bond-forming reaction (e.g., an olefination reaction (e.g., Horner-Wadsworth-Emmons olefination), Dieckmann reaction, catalytic Ring-Closing Olefin Metathesis, or Nozaki-Hiyama-Kishi reaction) to afford a macrocyclic intermediate. The invention also provides compounds useful as intermediates in the synthesis of eribulin or a pharmaceutically acceptable salt thereof and methods for preparing the same.

COMPOUNDS USEFUL IN THE SYNTHESIS OF HALICHONDRIN B ANALOGS

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, (2011/08/06)

In general, the invention features compounds useful for the synthesis of analogs of halichondrin B, such as eribulin or pharmaceutically acceptable salts thereof, e.g., eribulin mesylate. Exemplary compounds are of formula (I), (II), or (III):

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