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

Base Information

Chemical Name:tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4,5-dihydroxy pentyl carbamate
CAS No.:921201-41-4
Molecular Formula:C₂₀H₃₁NO₇
Molecular Weight:397.469
Hs Code.:

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

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

Chemical Property:

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

There total 4 articles about tert-butyl-(1S,3S,4S)-1-(ethoxycarbonyl)-3-(benzyloxy)-4,5-dihydroxy 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: 80.0%

: 921201-40-3
tert-butyl-(1S,3S)-1-(ethoxycarbonyl)-3-(benzyloxy)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl carbamate

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

Guidance literature:: With pyridinium p-toluenesulfonate; In ethanol; at 50 - 55 ℃; for 24h;
DOI:10.1016/j.tetasy.2006.10.033

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With 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

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

Guidance literature:: Multi-step reaction with 2 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

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