(2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

Base Information

• Chemical Name: (2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate
• CAS No.: 152996-71-9
• Molecular Formula: C₂₁H₃₇NO₄Si
• Molecular Weight: 395.615
• Mol file: 152996-71-9.mol

Synonyms:(2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

Chemical Property of (2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

There total 5 articles about (2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate 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:

(2S,3R)-N-Benzyloxy-2-(4-methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-butyramide (152996-70-8) → (2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate (152996-71-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol; for 2h; Yield given; Ambient temperature; pH = 7;

DOI:10.1016/S0040-4020(01)87214-8

Reference yield:

(2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol (152996-67-3) → (2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate (152996-71-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 69.8 percent / 4 Angstroem molecular sieves, 1 M p-toluenesulfonic acid monohydrate / propan-2-ol

3: Jones reagent / acetone / 0.33 h

4: 1.) N-hydroxybenzotriazole hydrate, DCC; 2.) triethylamine / 1.) CH₃CN, 1 h, r.t; 2.) overnight, r.t.

5: DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / Ambient temperature; pH = 7

With 2,6-dimethylpyridine; jones reagent; 4 A molecular sieve; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; isopropyl alcohol; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)87214-8

Reference yield:

(2S,3R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-butyric acid → (2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate (152996-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) N-hydroxybenzotriazole hydrate, DCC; 2.) triethylamine / 1.) CH₃CN, 1 h, r.t; 2.) overnight, r.t.

2: DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / Ambient temperature; pH = 7

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)87214-8

upstream raw materials:

(2S,3R)-N-Benzyloxy-2-(4-methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-butyramide

(2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol

(2S,3R)-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-3-<(tri-i-propylsilyl)oxy>butan-1-ol

(2R,3R)-1-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-3-<(tri-i-propylsilyl)oxy>butane

Downstream raw materials:

(S)-1-Benzyloxy-3-((R)-1-hydroxy-ethyl)-azetidin-2-one

(3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone

(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone