Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate

Base Information

• Chemical Name: Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate
• CAS No.: 153011-60-0
• Molecular Formula: C₂₁H₂₈O₄Si
• Molecular Weight: 372.536
• Mol file: 153011-60-0.mol

Synonyms:Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate

Chemical Property of Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate

There total 3 articles about Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate 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: 94.0%

methanol (67-56-1) + (5S)-<1'-<(tert-Butyldiphenylsilyl)oxy>ethyl>-2,2-cyclohexylidene-1,3-dioxolan-4-one (153011-59-7) → Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate (153011-60-0)

Guidance literature:

With sodium methylate; at 0 ℃; for 0.25h;

DOI:10.1021/jo00079a022

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) + (S)-2,4-dihydroxybutyric acid methyl ester (154006-52-7) → Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate (153011-60-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(02)01290-5

Reference yield:

(2S)-2-hydroxy-butanedioic acid 1-mono methyl ester (66212-45-1) → Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate (153011-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

2: triethylamine; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; dimethylsulfide borane complex; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(02)01290-5

upstream raw materials:

methanol

(5S)-<1'-<(tert-Butyldiphenylsilyl)oxy>ethyl>-2,2-cyclohexylidene-1,3-dioxolan-4-one

tert-butylchlorodiphenylsilane

(S)-2,4-dihydroxybutyric acid methyl ester

Downstream raw materials:

(2S)-4-O-(tert-butyldiphenylsilyl)butane-1,2,4-triol

(S)-4-(tert-butyldiphenylsiloxy)-2-(triethylsiloxy)butyric acid methyl ester

(S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanal

(S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanol