tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

Base Information

Chemical Name:tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate
CAS No.:921201-43-6
Molecular Formula:C₂₆H₄₅NO₇Si
Molecular Weight:511.731
Hs Code.:

Synonyms:tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

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Chemical Property of tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

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Technology Process of tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

There total 5 articles about tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate 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: 96.0%

: 921201-41-4
tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4,5-dihydroxy pentyl carbamate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 921201-43-6
tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1016/j.tetasy.2006.10.033

Reference yield:

: tert-butoxycarbonylamino-(ethoxy-ethoxymethyl-phosphinoyl)-acetic acid ethyl ester

: 921201-43-6
tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium tert-butoxide / CH₂Cl₂ / 0.5 h / cooling

1.2: CH₂Cl₂ / 5 h / 20 °C

2.1: 74 percent / Na₂CO₃; hydrogen / palladium on carbon / ethyl acetate / 3 h / atmospheric pressure

3.1: 80 percent / pyridinium para-toluenesulfonate / ethanol / 24 h / 50 - 55 °C

4.1: 96 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; sodium carbonate; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate; 1.2: Wittig-Horner reaction;
DOI:10.1016/j.tetasy.2006.10.033

Reference yield:

: 921201-39-0
tert-butyl (S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-enyl carbamate

: 921201-43-6
tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4-hydroxy-5-(tert-butyl dimethyl silyloxy)-pentyl carbamate

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / Na₂CO₃; hydrogen / palladium on carbon / ethyl acetate / 3 h / atmospheric pressure

2: 80 percent / pyridinium para-toluenesulfonate / ethanol / 24 h / 50 - 55 °C

3: 96 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; hydrogen; pyridinium p-toluenesulfonate; sodium carbonate; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;
DOI:10.1016/j.tetasy.2006.10.033