(2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester
• CAS No.: 277318-43-1
• Molecular Formula: C₁₆H₂₄O₃S
• Molecular Weight: 296.431
• Mol file: 277318-43-1.mol

Synonyms:(2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester

Chemical Property of (2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester

There total 1 articles about (2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl 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:

tert-butyl (phenylthio)acetate (63006-68-8) + isobutyraldehyde (78-84-2) → (2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester (277318-43-1) + 3-hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester

Guidance literature:

tert-butyl (phenylthio)acetate; With diazaborolidine; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 5h;

isobutyraldehyde; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)00302-6

Reference yield: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester (277318-43-1) → 3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)00302-6

Reference yield:

(2S,3S)-3-Hydroxy-4-methyl-2-phenylsulfanyl-pentanoic acid tert-butyl ester (277318-43-1) → (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-2-phenylsulfanyl-pentanal

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: DIBAL / toluene / -78 °C

3: PDC; MS, 4 Angstroem / CH₂Cl₂

With 2,6-dimethylpyridine; dipyridinium dichromate; 4 A molecular sieve; diisobutylaluminium hydride; In dichloromethane; toluene; 1: Alkylation / 2: Reduction / 3: Oxidation;

DOI:10.1016/S0040-4039(00)00302-6

upstream raw materials:

tert-butyl (phenylthio)acetate

isobutyraldehyde