3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester

Base Information

• Chemical Name: 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester
• CAS No.: 251556-95-3
• Molecular Formula: C₂₈H₅₀O₃SSi₂
• Molecular Weight: 522.94
• Mol file: 251556-95-3.mol

Synonyms:3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester

Chemical Property of 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester

There total 8 articles about 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester 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%

phenylmethanethiol (100-53-8) + (S)-4-Benzyl-3-[(3S,4S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enoyl]-oxazolidin-2-one (251556-94-2) → 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester (251556-95-3)

Guidance literature:

phenylmethanethiol; With n-butyllithium; In tetrahydrofuran; at 0 ℃;

(S)-4-Benzyl-3-[(3S,4S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enoyl]-oxazolidin-2-one; In tetrahydrofuran; for 0.333333h;

DOI:10.1055/s-1999-2888

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester (251556-95-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 50 °C

2.1: 90 percent / Raney-Ni / tetrahydrofuran / 1.5 h / Heating

3.1: n-BuLi / tetrahydrofuran / 0 °C

3.2: 85 percent / tetrahydrofuran / 0.33 h

With 2,6-dimethylpyridine; n-butyllithium; nickel; In tetrahydrofuran; dichloromethane; 1.1: Substitution / 2.1: Reduction / 3.1: Metallation / 3.2: Substitution;

DOI:10.1055/s-1999-2888

Reference yield:

(2R,3R)-3-(tert-butyldimethylsilyloxy)-2,4-dimethylpent-4-enal (171013-57-3) → 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enethioic acid S-benzyl ester (251556-95-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: CH₂Cl₂ / -78 - 20 °C

2.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 50 °C

3.1: 90 percent / Raney-Ni / tetrahydrofuran / 1.5 h / Heating

4.1: n-BuLi / tetrahydrofuran / 0 °C

4.2: 85 percent / tetrahydrofuran / 0.33 h

With 2,6-dimethylpyridine; n-butyllithium; nickel; In tetrahydrofuran; dichloromethane; 1.1: Addition / 2.1: Substitution / 3.1: Reduction / 4.1: Metallation / 4.2: Substitution;

DOI:10.1055/s-1999-2888

upstream raw materials:

phenylmethanethiol

(S)-4-Benzyl-3-[(3S,4S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-6-enoyl]-oxazolidin-2-one

t-butyldimethylsiyl triflate

(2R,3R)-3-(tert-butyldimethylsilyloxy)-2,4-dimethylpent-4-enal