(2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol

Base Information

• Chemical Name: (2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol
• CAS No.: 223437-37-4
• Molecular Formula: C₂₆H₃₈O₂Si₂
• Molecular Weight: 438.758
• Mol file: 223437-37-4.mol

Synonyms:(2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol

Chemical Property of (2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol

There total 5 articles about (2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-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: 52.0%

BF3·Et2O + (2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane (223437-33-0) + trimethylsilylacetylene (1066-54-2) → (2S,3R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol (223437-39-6) + (2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol (223437-37-4)

Guidance literature:

With n-butyllithium; ammonium chloride; In tetrahydrofuran;

Reference yield: 52.0%

(2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane (223437-33-0) + trimethylsilylacetylene (1066-54-2) → (2S,3R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol (223437-39-6) + (2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol (223437-37-4)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.333333h;

(2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.833333h;

DOI:10.1021/jm000261j

Reference yield:

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8) → (2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-6-(trimethylsilyl)hex-5-yn-3-ol (223437-37-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DMSO; oxalyl chloride; Et₃N / -78 - 0 °C

2.1: 92 percent / tetrahydrofuran; hexane / 0.75 h / 20 °C

3.1: 100 percent / mCPBA / CH₂Cl₂

4.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

4.2: 52 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 0.83 h / -78 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;

DOI:10.1021/jm000261j

upstream raw materials:

(2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane

trimethylsilylacetylene

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester