(1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol

Base Information

• Chemical Name: (1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol
• CAS No.: 219308-63-1
• Molecular Formula: C₂₇H₃₆O₄Si
• Molecular Weight: 452.666
• Mol file: 219308-63-1.mol

Synonyms:(1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol

Chemical Property of (1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol

There total 4 articles about (1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol 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: 77.0%

(3S,3aS,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5,5-dimethoxy-2,3,3a,4,5,7a-hexahydro-inden-1-one (219308-56-2) → (1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol (219308-63-1) + (1S,6S,7S,9R)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol

Guidance literature:

With sodium tetrahydroborate; In methanol; at -78 ℃; for 3h; Yields of byproduct given;

DOI:10.1021/ja982596k

Reference yield:

(S)-4-hydroxycyclopent-2-en-1-one (59995-47-0,61305-27-9,61740-29-2,59995-49-2) → (1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol (219308-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 1.) BHT, 2.) pyridinium p-toluenosulfonate / 1.) xylene, 140 deg C, 10 h, 2.) methanol, RT, 2 h

3: NaBH₄ / methanol / 3 h / -78 °C

With dmap; sodium tetrahydroborate; 2,6-di-tert-butyl-4-methyl-phenol; pyridinium p-toluenesulfonate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja982596k

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1S,6S,7S,9S)-4,4-dimethoxy-7-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en-9-ol (219308-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 1.) BHT, 2.) pyridinium p-toluenosulfonate / 1.) xylene, 140 deg C, 10 h, 2.) methanol, RT, 2 h

3: NaBH₄ / methanol / 3 h / -78 °C

With dmap; sodium tetrahydroborate; 2,6-di-tert-butyl-4-methyl-phenol; pyridinium p-toluenesulfonate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja982596k

upstream raw materials:

(3S,3aS,7aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5,5-dimethoxy-2,3,3a,4,5,7a-hexahydro-inden-1-one

(S)-4-hydroxycyclopent-2-en-1-one

tert-butylchlorodiphenylsilane

4(S)-<(tert-butyldiphenylsilyl)oxy>cyclopent-2-en-1-one

Downstream raw materials:

(1S,6S,7S,9R)-4,4-dimethoxy-7,9-bis-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-3-en

(1S,6S,7S,9R)-7,9-bis-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-2-en-4-one

methyl 2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-(carboxaldehyde)-1β-cyclopentane>-acetate

(1S,2R,3R,6S,7S,9R)-2,3-dihydroxy-7,9-bis-<(tert-butyldiphenylsilyl)oxy>bicyclo<4.3.0>non-4-one