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

Base Information

• Chemical Name: (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-5-(methoxymethoxy)-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadiene
• CAS No.: 129264-70-6
• Molecular Formula: C₃₂H₅₀O₄Si₂
• Molecular Weight: 554.918
• Mol file: 129264-70-6.mol

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

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

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>-5-(methoxymethoxy)-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadiene

There total 5 articles about (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-5-(methoxymethoxy)-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadiene 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: 85.0%

(2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadien-5-ol (129264-69-3) + chloromethyl methyl ether (107-30-2) → (2S,4R,5S,6E,8E)-1-<(tert-butyldiphenylsilyl)oxy>-5-(methoxymethoxy)-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadiene (129264-70-6)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h; Ambient temperature;

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>-5-(methoxymethoxy)-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadiene (129264-70-6)

Guidance literature:

Multi-step reaction with 5 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

5: 85 percent / diisopropylethylamine, dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; n-butyllithium; L-Selectride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

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>-5-(methoxymethoxy)-4-methyl-2-<(trimethylsilyl)oxy>-6,8-decadiene (129264-70-6)

Guidance literature:

Multi-step reaction with 4 steps

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

4: 85 percent / diisopropylethylamine, dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; L-Selectride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00309a022

upstream raw materials:

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

chloromethyl methyl ether

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

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

Downstream raw materials:

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

(2S,4R,5S,6E,8E)-1-<<(2',4',6'-triisopropylphenyl)-sulfonyl>oxy>-5-(methoxymethoxy)-4-methyl-6,8-decadien-2-ol

O-benzyldihydromevinolin

(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