(2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate

Base Information

• Chemical Name: (2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate
• CAS No.: 159801-09-9
• Molecular Formula: C₃₁H₄₆N₂O₈Si
• Molecular Weight: 602.8
• Mol file: 159801-09-9.mol

Synonyms:(2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate

Chemical Property of (2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate

There total 2 articles about (2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate 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:

(R)-dimethyl malate (70681-41-3) → (2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate (159801-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

2: 41 percent / 1.) lithium di-iso-propylamide / tetrahydrofuran; hexane / 1.) -60 deg C -> -30 deg C (during 80 min.); 2.) -60 deg C, 20 min.

With 1H-imidazole; lithium diisopropyl amide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89308-X

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate (159801-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

2: 41 percent / 1.) lithium di-iso-propylamide / tetrahydrofuran; hexane / 1.) -60 deg C -> -30 deg C (during 80 min.); 2.) -60 deg C, 20 min.

With 1H-imidazole; lithium diisopropyl amide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89308-X

Reference yield: 85.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (2S,3R) methyl 4-<(tert-butyldiphenylsilyl)oxy>-2--3-hydroxybutanoate (159801-09-9) → (2S,3R) benzyl 2--4-<(tert-butyldiphenylsilyl)oxy>-3-hydroxybutanohydroxamate (159801-11-3)

Guidance literature:

With trimethylaluminum; In tetrahydrofuran; toluene; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89308-X

upstream raw materials:

(R)-dimethyl malate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2S,3R) benzyl 2--4-<(tert-butyldiphenylsilyl)oxy>-3-hydroxybutanohydroxamate

(3S,4S) 1-(benzyloxy)-3--4-<(tert-butyldiphenylsilyloxy)methyl>-2-azetidinone

(3S,4S) 1-(benzyloxy)-3--4-hydroxymethyl-2-azetidinone