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
• Mol file: 123975-54-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate (60079-12-1) + allyl bromide (106-95-6) → t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-(2S)-hex-5-enoate (123975-54-2,123975-55-3)

Guidance literature:

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

Reference yield: 2.0%

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate (60079-12-1) + allyl bromide (106-95-6) → t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-(2S,3S)-hex-5-enoate + tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate (123975-54-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 25 ℃; for 1h;

DOI:10.1016/0040-4020(95)00454-G

Reference yield:

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester (47307-26-6,149967-07-7) → t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-(2S)-hex-5-enoate (123975-54-2,123975-55-3)

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

upstream raw materials:

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate

allyl bromide

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester

N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester

Downstream raw materials:

2-((S)-1-(benzyloxycarbonylamino)-2-tert-butoxy-2-oxoethyl)pent-4-enoic acid

(2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester

(2S,3R,5R)-5-Hydroxy-pyrrolidine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester

(2S,3R)-2-Benzyloxycarbonylamino-3-(2-oxo-ethyl)-succinic acid 1-tert-butyl ester 4-methyl ester