(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

Base Information

Chemical Name:(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol
CAS No.:1647153-54-5
Molecular Formula:C₂₀H₃₅NO₄Si
Molecular Weight:381.588
Hs Code.:

Synonyms:(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

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Chemical Property of (2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

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Technology Process of (2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

There total 4 articles about (2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol 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: 74.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 188802-11-1
(2R,3S)-2-Amino-1-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentan-3-ol

: 1647153-54-5
(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

Guidance literature:: With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 16h;
DOI:10.3762/bjoc.10.113

Reference yield:

: 188840-00-8
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde

: 1647153-54-5
(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1: tetrahydrofuran; diethyl ether

2: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol

3: sodium carbonate / water; 1,4-dioxane / 16 h / 0 - 20 °C

With 10 wt% Pd(OH)2 on carbon; hydrogen; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; water; 1: |Grignard Reaction;
DOI:10.3762/bjoc.10.113

Reference yield:

: 188802-16-6
(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propan-1-ol

: 1647153-54-5
(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane

2: tetrahydrofuran; diethyl ether

3: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol

4: sodium carbonate / water; 1,4-dioxane / 16 h / 0 - 20 °C

With oxalyl dichloride; 10 wt% Pd(OH)2 on carbon; hydrogen; sodium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; 1: |Swern Oxidation / 2: |Grignard Reaction;
DOI:10.3762/bjoc.10.113