90741-27-8

Basic information

• Product Name: (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate
• Synonyms: (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate;L-Proline,5-oxo-1-(phenylMethyl)-, 1,1-diMethylethyl ester;5-Oxo-1-(phenylmethyl)-L-proline 1,1-dimethylethyl ester
• CAS NO: 90741-27-8
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.34284
• Mol File: 90741-27-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 73-74℃
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate(90741-27-8)
• EPA Substance Registry System: (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate(90741-27-8)

Safety Data

• Hazardous Substances Data: 90741-27-8(Hazardous Substances Data)

Usage

General Description

(S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate is a chemical substance with a specific stereochemistry, implied by the (S) prefix. It belongs to a class of compounds known as pyrrolidines, which are four-membered heterocyclic compounds containing a nitrogen atom. This chemical has two functional groups, a carboxylate group and a benzyl group. The carboxylate group is attached to a tertiary butyl (tert-butyl) group, a type of alkyl group. The benzyl group gives the molecule its aromatic property. Although there is no specific information about its uses, compounds in this class often serve as intermediates in the synthesis of other chemicals, in pharmaceuticals, or in material science.

Upstream product

• 38854-94-3 N-benzyl-L-pyroglutamic acid 
• 75-65-0 tert-butyl alcohol 
• 77539-18-5 (S)-(+)-2-benzylamino glutaric acid 
• 100-52-7 benzaldehyde 
• 56-86-0 L-glutamic acid 
• 540-88-5 acetic acid tert-butyl ester 
• 35418-16-7 L-t-butyl pyroglutamate 
• 100-39-0 benzyl bromide 
• 90741-31-4 (S)-N-benzyl-5-thioxoproline tert-butyl ester 
• 172172-35-9 Trifluoro-methanesulfonic acid 6-methyl-2-oxo-tetrahydro-pyran-3-yl ester 

Downstream Products

• 90741-33-6 (2S)-1-benzyl-(E)-5-<(methoxycarbonyl)methylidene>proline tert-butyl ester 
• 90741-31-4 (S)-N-benzyl-5-thioxoproline tert-butyl ester 
• 90741-40-5 tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate 
• 90741-37-0 (2S)-cis-1-benzyl-5-(carboxymethyl)proline tert-butyl ester 
• 90741-38-1 (2S)-cis-1-benzyl-5-((methoxycarbonyl)methyl)proline 
• 90741-36-9 (2R-cis)-5-((1,1-Dimethylethoxy)carbonyl)-1-(phenylmethyl)-2-pyrrolidineacetic acid methyl ester 
• 90762-72-4 (2R)-1-benzyl-2-((methoxycarbonyl)methyl)pyrrolidine 
• 643014-12-4 diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 
• 643014-14-6 diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(2-benzyloxycarbonylaminoacetamido)-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 
• 643014-10-2 diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 

Relevant articles and documents

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Regioselective reduction of β-enaminoesters

The regioselective reduction of β-enaminoesters derived from pyroglutamic acid can be readily achieved under mild conditions. Copyright Taylor & Francis, Inc.

A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries

9-(S)-Pyroglutaminyl-β-carbolines were allowed to react with a nucleophile (allyltributyltin or a silyl enol ether) in the presence of 2,2,2-trichloroethyl chloroformate to give 1,2-addition products in good yields and high diastereoselectivity. The chiral auxiliary at N-9 was readily removed by a mild hydrolysis. The same chiral source afforded both enantiomers by simply altering a protecting group of the amide nitrogen. That is, (S)-pyroglutaminyl groups which had an N-alkyl group afforded the (S) isomer, whereas the ones having an N-acyl group produced the (R) isomer of the addition products.