t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate

Base Information

Chemical Name:t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate
CAS No.:123999-77-9
Molecular Formula:C₂₀H₂₉NO₇
Molecular Weight:395.453
Hs Code.:

Synonyms:t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate

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Chemical Property of t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate

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Technology Process of t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate

There total 6 articles about t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate 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: 55.0%

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

: 123-38-6
propionaldehyde

: 123999-77-9
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate

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

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 123999-77-9
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 77 percent / potassium carbonate / H₂O; diethyl ether / 4 h / Ambient temperature

2: 95 percent / conc. sulphuric acid / CH₂Cl₂ / 48 h / Ambient temperature

3: 84 percent / tetrakis(triphenylphosphine)-palladium⁽⁰⁾, triphenylphosphine, pyrrolidine / CH₂Cl₂ / 0.17 h / Ambient temperature

4: 69 percent / diethyl ether / 1 h / Ambient temperature

5: 1.) bis(trimethylsilyl)amine, BuLi / 1.) THF, r.t., 10 min; 2.) THF, -30 - -40 deg C, 45 min; 3.) -78 deg C, 15 min

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sulfuric acid; potassium carbonate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether; dichloromethane; water;
DOI:10.1016/S0040-4020(01)85141-3

Reference yield:

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

: 123999-77-9
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-(2S)-hexanoate

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.) -78 deg C, 15 min

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether;
DOI:10.1016/S0040-4020(01)85141-3