(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
Hs Code.:

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

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

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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:

: 152996-70-8
(2S,3R)-N-Benzyloxy-2-(4-methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-butyramide

: 152996-71-9
(2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

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:

: 152996-67-3
(2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol

: 152996-71-9
(2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

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

: 152996-71-9
(2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

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