(2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane

Base Information

• Chemical Name: (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane
• CAS No.: 117438-72-9
• Molecular Formula: C₁₇H₃₀OSSi
• Molecular Weight: 310.576
• Mol file: 117438-72-9.mol

Synonyms:(2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane

Chemical Property of (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane

There total 4 articles about (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane 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: 99.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S)-3-methyl-4-(phenylsulfanyl)butan-2-ol (628315-68-4) → (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane (117438-72-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.tetasy.2004.07.049

Reference yield: 88.0%

(2S,3S)-3-<(tert-bytyldimethylsilyl)oxy>-2-methylbutyl methanesulfonate (117469-82-6) + thiophenol (108-98-5) → (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane (117438-72-9)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

DOI:10.1021/jo00260a020

Reference yield:

*,S*)>-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylbutanoic acid ethyl ester (85576-58-5) → (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2-methyl-1-(phenylthio)butane (117438-72-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / toluene; hexane / 2 h / -78 °C

2: 89 percent / pyridine / 20 h / Ambient temperature

3: 88 percent / t-BuOK / dimethylformamide / 1.5 h / Ambient temperature

With potassium tert-butylate; diisobutylaluminium hydride; In pyridine; hexane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00260a020

upstream raw materials:

sodium thiophenolate

(2S,3S)-3-<(tert-bytyldimethylsilyl)oxy>-2-methylbutyl methanesulfonate

thiophenol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(1S,2S)-(3-benzenesulfonyl-1,2-dimethyl-tetradecyloxy)-tert-butyl-dimethylsilane

(2S,3S)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1-(phenylsulfonyl)butane

C₄₁H₆₆O₁₀SSi

tert-butyl 4-<5(S)-<3-(phenylsulfonyl)-5(S)-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4(R)-methylhexyl>-3(S),4(R)-(cyclohexylidenedioxy)tetrahydropyran-2(S)-yl>-3-methyl-2(E)-butenoate