(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

Base Information

Chemical Name:(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine
CAS No.:1647153-55-6
Molecular Formula:C₂₃H₃₉NO₄Si
Molecular Weight:421.652
Hs Code.:

Synonyms:(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

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Chemical Property of (4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

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Technology Process of (4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

There total 5 articles about (4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine 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: 79.0%

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

: 77-76-9
2,2-dimethoxy-propane

: 1647153-55-6
(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

Guidance literature:: With 10-camphorsufonic acid; magnesium sulfate; at 50 ℃; for 27h; Inert atmosphere;
DOI:10.3762/bjoc.10.113

Reference yield:

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

: 1647153-55-6
(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

Guidance literature:: Multi-step reaction with 5 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

5: 10-camphorsufonic acid; magnesium sulfate / 27 h / 50 °C / Inert atmosphere

With oxalyl dichloride; 10 wt% Pd(OH)2 on carbon; 10-camphorsufonic acid; hydrogen; sodium carbonate; magnesium sulfate; 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

Reference yield:

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

: 1647153-55-6
(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

Guidance literature:: Multi-step reaction with 4 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

4: 10-camphorsufonic acid; magnesium sulfate / 27 h / 50 °C / Inert atmosphere

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