(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate
• CAS No.: 944154-87-4
• Molecular Formula: C₂₀H₃₄O₄SSi
• Molecular Weight: 398.639
• Mol file: 944154-87-4.mol

Synonyms:(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate

Chemical Property of (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate

There total 9 articles about (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S)-(+)-toluene-4-sulfonic acid 3-hydroxy-2-methylhex-5-enyl ester (501015-40-3) → (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate (944154-87-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1002/chem.201102542

Reference yield: 92.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,3S)-3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-1-ol (944154-96-5) → (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate (944154-87-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1016/j.tetlet.2007.04.069

Reference yield:

p-Toluolsulfonsaeure-<(R)-3-hydroxy-2-methylpropyl>ester → (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate (944154-87-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 10 - 20 °C / Inert atmosphere

2.1: diethyl ether / -78 °C / Inert atmosphere

2.2: 12 h / -78 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 72 h / 20 °C

With 1H-imidazole; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In diethyl ether; dichloromethane;

DOI:10.1002/chem.201102542

upstream raw materials:

p-toluenesulfonyl chloride

(2S,3S)-3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-1-ol

(R)-4-benzyl-3-((2R,3S)-3-hydroxy-2-methylhex-5-enoyl)oxazolidin-2-one

(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enoyl) oxazolidin-2-one

Downstream raw materials:

C₂₁H₃₄O₆SSi