129430-95-1

Basic information

• Product Name: cis-4-hydroxy-O-(4-tolylsulfonyl)-N-triphenylmethyl-L-proline methyl ester
• Synonyms: cis-4-hydroxy-O-(4-tolylsulfonyl)-N-triphenylmethyl-L-proline methyl ester
• CAS NO: 129430-95-1
• Molecular Weight: 541.668
• Mol File: 129430-95-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: cis-4-hydroxy-O-(4-tolylsulfonyl)-N-triphenylmethyl-L-proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: cis-4-hydroxy-O-(4-tolylsulfonyl)-N-triphenylmethyl-L-proline methyl ester(129430-95-1)
• EPA Substance Registry System: cis-4-hydroxy-O-(4-tolylsulfonyl)-N-triphenylmethyl-L-proline methyl ester(129430-95-1)

Safety Data

• Hazardous Substances Data: 129430-95-1(Hazardous Substances Data)

Upstream product

• 80514-79-0 trans-N-trityl-4-hydroxy-L-proline 
• 129430-93-9 (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 98-59-9 p-toluenesulfonyl chloride 
• 124456-35-5 5-triphenylmethyl-2-oxa-5-aza-bicyclo<2.2.1>heptan-3-one 

Relevant articles and documents

Simple Synthesis of cis-4-Hydroxy-L-proline and Derivatives Suitable for Use as Intermediates in Peptide Synthesis

An intramolecular Mitsunobu reaction in the presence of triphenylphosphine - diethyl azodicarboxylate (TPP-DEAD) resulted in the conversion of trans-4-hydroxy-N-trityl-L-proline to 5-triphenylmethyl-2-oxa-5-aza-bicycloheptan-3-one.This bicyclic lactone proved to be a key intermediate in the synthesis of cis-4-hydroxy-L-proline and derivatives thereof.TPP-DEAD-catalysed methanolysis of the key lactone gave the methyl ester of cis-4-hydroxy-N-trityl-L-proline, while ammonolysis in isopropyl alcohol provided the corresponding amide. p-Toluene-sulfonic acid treatmen t of the lactone, ester and amide led to detritylation and formation of the corresponding p-toluenesulfonates.Saponification of the key intermediate provided cis-4-hydroxy-N-trityl-L-proline which was first benzylated and then elaborated to the 1-hydroxybenzotriazolyl ester.This last ester and the three p-tolenesulfonates preparared above were utilised for the incorporation of cis-4-hydroxy-L-proline in the synthesis of model peptides.