N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

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Chemical Name:N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester
CAS No.:288582-37-6
Molecular Formula:C₂₇H₃₄N₂O₇
Molecular Weight:498.576
Hs Code.:

Synonyms:N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

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Chemical Property of N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

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Technology Process of N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

There total 1 articles about N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester 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: 68.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 133099-79-3
D-serine benzyl ester

: 89813-47-8
N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

: 288582-37-6
N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

Guidance literature:: trifluoromethylsulfonic anhydride; N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester; With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -20 ℃; for 0.75h;

D-serine benzyl ester; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -20 - -8 ℃; Further stages.;
DOI:10.1021/jo000071g

Reference yield: 27.0%

: 146432-42-0
2-[bis(benzyloxycarbonylmethyl)amino]ethyl bromide

: 288582-37-6
N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

: 288582-38-7
N-[2-bis[(benzyloxycarbonyl)methyl]aminoethyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

Guidance literature:: With phosphate buffer; In water; acetonitrile; pH=8; Heating;
DOI:10.1021/jo000071g

Reference yield:

: 288582-37-6
N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-D-serine benzyl ester

: (2S,4S)-4-{((R)-1-Benzyloxycarbonyl-2-hydroxy-ethyl)-[2-(bis-benzyloxycarbonylmethyl-amino)-ethyl]-amino}-pyrrolidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 27 percent / phosphate buffer / acetonitrile; H₂O / pH 8 / Heating

2: CF₃COOH / CH₂Cl₂ / 20 °C

With phosphate buffer; trifluoroacetic acid; In dichloromethane; water; acetonitrile; 1: Alkylation / 2: carbamate cleavage;
DOI:10.1021/jo000071g