(2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol

Base Information

• Chemical Name: (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol
• CAS No.: 129264-69-3
• Molecular Formula: C₃₀H₄₆O₃Si₂
• Molecular Weight: 510.864
• Mol file: 129264-69-3.mol

Synonyms:(2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol

Chemical Property of (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol

There total 4 articles about (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-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: 62.0%

(2S,4R,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-one (109000-33-1) → (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol (129264-69-3)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.416667h;

DOI:10.1021/jo00309a022

Reference yield:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol (129264-69-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) diisopropylamine, BuLi / 1.) THF, -78 deg C, 30 min 2.) -78 deg C to rt, 20 min

4: 62 percent / L-Selectride / tetrahydrofuran / 0.42 h / -78 °C

With n-butyllithium; L-Selectride; diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jo00309a022

Reference yield:

(2R,4S)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-methyl-4-butanolide (103233-24-5) → (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol (129264-69-3)

Guidance literature:

Multi-step reaction with 3 steps

3: 62 percent / L-Selectride / tetrahydrofuran / 0.42 h / -78 °C

With L-Selectride; In tetrahydrofuran;

DOI:10.1021/jo00309a022

upstream raw materials:

(2S,4R,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-one

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

(2R,4S)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-methyl-4-butanolide

(3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate

Downstream raw materials:

(2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-5-(methoxymethoxy)-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadiene

(+)-Dihydromevinolin

(1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<1(R)-hydroxy-4(R)-(benzyloxy)cyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene

(1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<4(R)-(benzyloxy)-1-oxocyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene