<1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe...

Base Information

• Chemical Name: <1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe...
• CAS No.: 158586-27-7
• Molecular Formula: C₄₈H₈₀O₁₁Si₂
• Molecular Weight: 889.328

Synonyms:<1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe...

Chemical Property of <1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe...

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Technology Process of <1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe...

There total 24 articles about <1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe... 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:

p-Anisaldehyde dimethyl acetal (2186-92-7) → <1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe... (158586-27-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 83 percent / dl-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 25 °C

2: 84 percent / OsO₄, NMO, water / acetone / 20 h / 25 °C

3: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

4: 1.) t-BuOK, n-BuLi, 2.) B-(-)-methoxydiisopinocampheylborane, 3.) BF₃*OEt₂, 4.) aq. H₂O₂, aq. NaOH

5: 92 percent / imidazole / dimethylformamide / 3 h / 50 °C

6: 98 percent / DIBAL / CH₂Cl₂ / 0.5 h / 0 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 0.5 h

8: 46percent aq. HF / acetonitrile / 0.5 h / 25 °C

9: 46.8 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

10: 95 percent / OsO₄, NMO, water / acetone / 7 h / 25 °C

11: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.83 h / 25 °C

12: 1.) KN(SiMe₃)2, 2.) ZnCl₂

With 1H-imidazole; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; water; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1246/bcsj.68.967

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → <1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe... (158586-27-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 46.8 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

2: 95 percent / OsO₄, NMO, water / acetone / 7 h / 25 °C

3: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.83 h / 25 °C

4: 1.) KN(SiMe₃)2, 2.) ZnCl₂

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1246/bcsj.68.967

Reference yield:

(2R,3S,4R)-4-methyl-2-(triethylsilyloxy)-5-hexen-3-ol (158586-21-1) → <1(2R,3S,4R,6S),2S,3S,4R,4(2S,3S,4S,5R,6R)>-1-<6-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylterahydropyran-2-yl>-3-hydroxy-4-<4-(4-methoxybenzyloxy)-3,5-dimethyl-6-<(2-trimethylsilylethoxy)methoxy>tetrahydropyran-2-yl>-2-methyl-1-pe... (158586-27-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 55 percent / CSA / hexane / 72 h / 25 °C

2: 1.) BH₃*SMe₂, cyclohexene, 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 51 deg C, 20 min

3: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / 25 °C

4: benzene / 12 h / 45 °C

5: 100 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 25 °C

6: 95 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.5 h / 25 °C

7: 70 percent / benzene; diethyl ether / 2 h / -78 °C

8: 92 percent / L-selectride / tetrahydrofuran / 1 h / -100 °C

9: OsO₄, NMO, water / acetone / 12 h / 25 °C

10: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

11: 48.5 percent / imidazole / dimethylformamide / 12 h / 40 °C

12: 1.) KN(SiMe₃)2, 2.) ZnCl₂

With pyridine; 1H-imidazole; sodium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; potassium hexamethylsilazane; L-Selectride; Dess-Martin periodane; zinc(II) chloride; cyclohexene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1246/bcsj.68.967

upstream raw materials:

(2-trimethylsilylethoxy)methyl 2,4,6-trideoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-heptodialdopyranoside-(1,5)

t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

p-Anisaldehyde dimethyl acetal

(2-trimethylethylsilylethoxy)methyl chloride

Downstream raw materials:

(2-trimethylsilylethoxy)methyl 2,4,6,8,12,13,14,15,16-nonadeoxy-3,11-di-O-(4-methoxybenzyl)-2,4,6,8,10,12-hexa-C-methyl-16-phenylsulfonyl-7-O-triethylsilyl-(14E)-D-threo-D-gluco-α-L-ido-hexadec-14-enos-9-uloside-(1,5)

(E)-(4S,5R,6S)-6-{(4R,5S,6R)-6-[(E)-(1S,3R,4S,5R)-9-Benzenesulfonyl-3-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5-trimethyl-2-oxo-non-7-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-5-(4-methoxy-benzyloxy)-4-methyl-hept-2-enoic acid ethyl ester

(E)-(5R,6S,7R,9S,10R,11S)-7-Hydroxy-6-(4-methoxy-benzyloxy)-11-[(2R,3S,4S,5R,6S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-6-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-5,7,9-trimethyl-8-oxo-10-triethylsilanyloxy-dodec-2-enoic acid ethyl ester

ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate

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