253776-38-4

Basic information

• Product Name: (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine
• Synonyms: (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine
• CAS NO: 253776-38-4
• Molecular Weight: 545.697
• Mol File: 253776-38-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine(253776-38-4)
• EPA Substance Registry System: (2R,3S,5S)-1-tert-butoxycarbonyl-2-tetrahydropyranyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine(253776-38-4)

Safety Data

• Hazardous Substances Data: 253776-38-4(Hazardous Substances Data)

Upstream product

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 116611-45-1 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 253776-34-0 (2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) 

Relevant articles and documents

A Versatile Method for the Facile Synthesis of Enantiopure trans-and cis-2,5-Disubstituted Pyrrolidines

Treatment of (2S)-1-O-benzylglycerol-2,3-bistriflate (2) with the trilithiated species of chiral building blocks 5-7 provided 2,3,5-trisubstituted pyrrolidines that were subjected to reductive desulfonylation to give trans-2,5-disubstituted pyrrolidines 11-13, respectively. The same reaction sequence with the (2R)-bistriflate 4 and trilithiated 5 afforded the eis isomer 19. This two-step synthetic mehodology can furnish any one of the four possible diastereomers of enantiopure 2,5-disubstituted pyrrolidines in 60-72% overall yields.