151265-55-3

Basic information

• Product Name: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-phenyl-, (2R,3R,4S,5S)-
• Synonyms: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-phenyl-, (2R,3R,4S,5S)-
• CAS NO: 151265-55-3
• Molecular Formula: C11H15 N O3
• Molecular Weight: 209.24
• Mol File: 151265-55-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-phenyl-, (2R,3R,4S,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-phenyl-, (2R,3R,4S,5S)-(151265-55-3)
• EPA Substance Registry System: 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-5-phenyl-, (2R,3R,4S,5S)-(151265-55-3)

Safety Data

• Hazardous Substances Data: 151265-55-3(Hazardous Substances Data)

Upstream product

• 1000612-60-1 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-1-hydroxy-5-phenylpyrrolidine 
• 201290-06-4 3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enitol 
• 16838-89-4 2,3,5-tri-O-benzyl-D-xylofuranose 
• 904893-23-8 (3S,4R,5R)-5-methanesulfonyloxy-3,4,6-tribenzyloxy-1-hexene 
• 904893-24-9 (-)-(2R,3R,4R)-1,3,4-tris(benzyloxy)-5-oxopentan-2-yl methanesulfonate 
• 904893-22-7 (2S,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide 
• 904893-25-0 (2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-phenyl-N-hydroxy-pyrrolidine 

Relevant articles and documents

Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A (20) and B (18) against α-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 μM, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases.

Radicamines A and B: Synthesis and revision of the absolute configuration

Starting from D-xylose, enantioselective syntheses of 1 and 2, the proposed structures for radicamines A and B, were accomplished. Both 1H and 13C NMR spectra of 1 and 2 were identical with those of the natural products, but the optical rotation measurements identified that 1 and 2 were actually the enantiomers of the natural radicamines A and B, respectively.