155102-96-8

Basic information

• Product Name: 2-Pyrrolidinone, 3,4-dihydroxy-5-(hydroxymethyl)-, (3R,4R,5R)- (9CI)
• Synonyms: 2-Pyrrolidinone, 3,4-dihydroxy-5-(hydroxymethyl)-, (3R,4R,5R)- (9CI)
• CAS NO: 155102-96-8
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.12926
• Product Categories: ALDEHYDE
• Mol File: 155102-96-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Pyrrolidinone, 3,4-dihydroxy-5-(hydroxymethyl)-, (3R,4R,5R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinone, 3,4-dihydroxy-5-(hydroxymethyl)-, (3R,4R,5R)- (9CI)(155102-96-8)
• EPA Substance Registry System: 2-Pyrrolidinone, 3,4-dihydroxy-5-(hydroxymethyl)-, (3R,4R,5R)- (9CI)(155102-96-8)

Safety Data

• Hazardous Substances Data: 155102-96-8(Hazardous Substances Data)

Upstream product

• 190902-25-1 (3S,4R,5R)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone 
• 293297-97-9 tert-butyl (2R,3R,4R)-2-({[(tert-butyl)dimethylsilyl]oxy}methyl)-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate 
• 157831-28-2 (3S,4R,5S)-3,4-dibenzyloxy-5-hydroxymethyl-pyrrolidin-2-one 
• 1064667-01-1 tert-butyl (4R)-4-[(1R,2S)-3-ethoxy-1,2-dihydroxy-3-oxopropyl]-2,2-dimethyloxazolidine-3-carboxylate 
• 190902-23-9 (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone 
• 190902-19-3 (1RS,2S,3R)-2,3-bis(methoxymethyl)oxy-4-(t-butyldimethylsilyl)oxy-1-cyano-N-(4-methoxybenzyl)butanamide 
• 190902-22-8 (3S,4R,5RS)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-methoxycarbonyl-2-pyrrolidinone 
• 190902-21-7 (3S,4R,5RS)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-cyano-2-pyrrolidinone 
• 190902-20-6 (1RS,2S,3R)-2,3-bis(methoxymethyl)oxy-4-hydroxy-1-cyano-N-(4-methoxybenzyl)butanamide 
• 158349-27-0 (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one 
• 154631-82-0 (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one 
• 108692-47-3 (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 

Relevant articles and documents

The use of J-coupling as a sole criterion to assign the total absolute stereochemistry of new pyrrolidinone class synthetic analogs, derived from S-pyroglutamic acid

During the synthesis of new pyrrolidinone analogs possessing biological activity it is intriguing to assign their absolute stereochemistry as it is well known that drug potency is influenced by the stereochemistry. The combination of J-coupling information with theoretical results was used in order to establish their total stereochemistry when the chiral center of the starting material has known absolute stereochemistry. The J-coupling can be used as a sole criterion for novel synthetic analogs to identify the right stereochemistry. This approach is extremely useful especially in the case of analogs whose 2D NOESY spectra cannot provide this information. Few synthetic examples are given to prove the significance of this approach.

Short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B and a formal synthesis of nectrisine

(Chemical Equation Presented) A short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B is reported. Garner's (R)-aldehyde, prepared from D-serine, was the chiral starting material. The pyrrolidine ring was stereoselectively created in a very efficient way through a five-step, one-pot transformation. In addition, an intermediate of this synthesis was transformed into an intermediate of a previously published synthesis of the potent α-glucosidase inhibitor nectrisine.

Process and intermediate compounds for the preparation of pyrrolidines

Processes for the preparation of pyrrolidones (7 and 8) and pyrrolidines (9 and 10) from tri-O-acetyl-D-erythro-4-pentulosonic acid esters are described. The compounds are aza sugar analogs of D-ribofuranoside and are intermediates to drugs which regulate nucleoside and nucleic acid synthesis.