N-Cbz-L-proline p-tolylthiol ester

Base Information

• Chemical Name: N-Cbz-L-proline p-tolylthiol ester
• CAS No.: 1059596-61-0
• Molecular Formula: C₂₀H₂₁NO₃S
• Molecular Weight: 355.458
• Mol file: 1059596-61-0.mol

Synonyms:N-Cbz-L-proline p-tolylthiol ester

Chemical Property of N-Cbz-L-proline p-tolylthiol ester

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of N-Cbz-L-proline p-tolylthiol ester

There total 1 articles about N-Cbz-L-proline p-tolylthiol 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: 65.0%

para-thiocresol (106-45-6) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → N-Cbz-L-proline p-tolylthiol ester (1059596-61-0)

Guidance literature:

With benzotriazol-1-ol; diisopropyl-carbodiimide; In ethyl acetate; at 0 - 20 ℃; for 24h;

DOI:10.1021/jo400797t

Reference yield: 70.0%

N-Cbz-L-proline p-tolylthiol ester (1059596-61-0) + tributyl(thien-2-yl)stannane (54663-78-4) → (S)-benzyl 2-(thiophene-5-carbonyl)pyrrolidine-1-carboxylate (1059597-26-0)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; ((diphenylphosphoryl)oxy)copper(I); triethyl phosphite; In tetrahydrofuran; hexane; at 23 ℃; optical yield given as %ee; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ol8018456

Reference yield:

N-Cbz-L-proline p-tolylthiol ester (1059596-61-0) + L-Ser-OEt hydrochloride → C18H24N2O6 (1310941-78-6)

Guidance literature:

L-Ser-OEt hydrochloride; With triethylamine; In tetrahydrofuran; at 20 ℃;

N-Cbz-L-proline p-tolylthiol ester; With N,O-bis-(trimethylsilyl)-acetamide; In ethanol; at 40 ℃; for 48h;

DOI:10.1039/c1gc15401j

upstream raw materials:

para-thiocresol

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

(S)-benzyl 2-(thiophene-5-carbonyl)pyrrolidine-1-carboxylate

C₁₈H₂₄N₂O₆

ethyl (N-benzoxycarbonyl-L-prolyl)glycinate

-L-leucine methyl ester

Refernces

• 1、 Chen, Hao,He, Maomao,Wang, Yaya,Zhai, Linhui,Cui, Yongbo,Li, Yangyan,Lee, Yan,Zhou, Haibing,Hong, Xuechuan,Deng, Zixin. "Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters". supporting information; experimental part. p. 2723 - 2726. Retrieved 2011/11/06.