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

Base Information

• Chemical Name: (2S,3R) benzyl 2--4-<(tert-butyldiphenylsilyl)oxy>-3-hydroxybutanohydroxamate
• CAS No.: 159801-11-3
• Molecular Formula: C₃₇H₅₁N₃O₈Si
• Molecular Weight: 693.913
• Mol file: 159801-11-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

Reference yield:

di-tert-butyl-diazodicarboxylate (870-50-8) → (2S,3R) benzyl 2--4-<(tert-butyldiphenylsilyl)oxy>-3-hydroxybutanohydroxamate (159801-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 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.

2: 85 percent / 2 M Me₃Al / toluene; tetrahydrofuran / 1 h / Ambient temperature

With trimethylaluminum; lithium diisopropyl amide; In tetrahydrofuran; hexane; toluene;

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

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3R) benzyl 2--4-<(tert-butyldiphenylsilyl)oxy>-3-hydroxybutanohydroxamate (159801-11-3)

Guidance literature:

Multi-step reaction with 3 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.

3: 85 percent / 2 M Me₃Al / toluene; tetrahydrofuran / 1 h / Ambient temperature

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

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

upstream raw materials:

O-benzylhydoxylamine hydrochloride

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

di-tert-butyl-diazodicarboxylate

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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