(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]

Base Information

• Chemical Name: (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]
• CAS No.: 253128-10-8
• Molecular Formula: C45H78O9SSi2
• Molecular Weight: 851.346
• Mol file: 253128-10-8.mol

Synonyms:ER 804028;

Chemical Property of (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]

Chemical Property:

• Boiling Point: 783.4±60.0 °C(Predicted)
• PKA: 15.06±0.10(Predicted)
• PSA: 118.13000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 10.74830

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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]

There total 100 articles about (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] which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

C52H90O12SSi2 (1316279-00-1) → 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 (253128-10-8)

Guidance literature:

C₅₂H₉₀O₁₂SSi₂; With pyridine; Methanesulfonic anhydride; In dichloromethane; at 0 - 20 ℃; for 1h;

With methanol; sodium methylate; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

Reference yield:

(2R,3S)-3-[2-(benzyloxy)ethyl]oxiran-2-methanol (126107-76-4) → 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)

Guidance literature:

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

With pyridine; 1H-imidazole; quinoline; chromium dichloride; hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; methylmagnesium bromide; potassium tert-butylate; hydrogen; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 13.1: Swern oxidation / 14.1: Nozaki-Hiyama-Kishi coupling;

DOI:10.1016/j.bmcl.2004.08.069

Reference yield:

(2S,3R)-2-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxymethyl)-oxirane (805246-98-4) → 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)

Guidance literature:

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

With pyridine; 1H-imidazole; quinoline; chromium dichloride; hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; methylmagnesium bromide; potassium tert-butylate; hydrogen; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; Lindlar's catalyst; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 12.1: Swern oxidation / 13.1: Nozaki-Hiyama-Kishi coupling;

DOI:10.1016/j.bmcl.2004.08.069

upstream raw materials:

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

thiophenol

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

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

Downstream raw materials:

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