tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate

Base Information

Chemical Name:tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate
CAS No.:123975-54-2
Molecular Formula:C₂₀H₂₇NO₆
Molecular Weight:377.437
Hs Code.:

Synonyms:tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate

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Chemical Property of tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate

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Technology Process of tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate

There total 6 articles about tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate 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: 45.0%

: 60079-12-1
β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate

: 106-95-6
allyl bromide

: 123975-54-2,123975-55-3
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-(2S)-hex-5-enoate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; further reagent;

Reference yield: 2.0%

: 60079-12-1
β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate

: 106-95-6
allyl bromide

: t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-(2S,3S)-hex-5-enoate

: 123975-54-2
tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 25 ℃; for 1h;
DOI:10.1016/0040-4020(95)00454-G

Reference yield:

: 47307-26-6,149967-07-7
(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester

: 123975-54-2,123975-55-3
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-(2S)-hex-5-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: 69 percent / diethyl ether / 1 h / Ambient temperature

2: 1.) bis(trimethylsilyl)amine, BuLi / 1.) THF, r.t., 10 min; 2.) THF, -30 - -40 deg C, 45 min; 3.) allowed to warm from -78 deg C to r.t., 1 h

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether;
DOI:10.1016/S0040-4020(01)85140-1