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

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

• 108692-47-3 (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 
• 190902-25-1 (3S,4R,5R)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone 
• 1064667-01-1 tert-butyl (4R)-4-[(1R,2S)-3-ethoxy-1,2-dihydroxy-3-oxopropyl]-2,2-dimethyloxazolidine-3-carboxylate 
• 157831-28-2 (3S,4R,5S)-3,4-dibenzyloxy-5-hydroxymethyl-pyrrolidin-2-one 
• 293297-97-9 tert-butyl (2R,3R,4R)-2-({[(tert-butyl)dimethylsilyl]oxy}methyl)-3,4-dihydroxy-5-oxopyrrolidine-1-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 

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.

Enantioselective Formal Synthesis of Nectrisine Using a Palladium-Catalyzed Asymmetric Allylic Amination and Cross-Metathesis as Key Steps

A formal enantioselective synthesis of nectrisine, a potent α-glucosidase inhibitor, was carried out starting from butadiene monoepoxide through a synthetic sequence involving enantioselective allylic substitution, cross-metathesis, dihydroxylation, and cyclization.

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.

Synthetic studies of carzinophilin. Part 3: Synthetic approach toward carzinophilin and successful synthesis of 13-O-desacetyl-12,13-di-O-benzyl-4-O-methylcarzinophilin

The synthetic procedures of the title compound (2), a protected form of carzinophilin (1), were developed. While efforts toward the total synthesis of 1 failed, comparison of the 1H NMR spectra of 2 and some other related compounds with that of

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.

Synthesis of nectrisine and related compounds, and their biological evaluation

An efficient and novel process is described for the synthesis of nectrisine 5 and its related derivatives 6,7 as potent glucosidase inhibitors via the corresponding lactams starting from D-(-)-diethyl tartrate. Also the results of biological evaluation of the synthesized compounds are described.

A Facile Transformation of Sugar Lactones to Azasugars

The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.

A short diastereoselective synthesis of the natural (2R, 3R, 4R)-2-hydroxymethyl-3,4-dihydroxypyrrolidine

1,4-Dideoxy-1,4-imino-D-arabinitol 1, a glycosidase inhibitor constituent of Arachniodes standishii 1 and angylocalyx boutiqueanus2 was synthesized from (S)-pyroglutamic acid through regioselective ring opening of the epoxide 3.

Structure and synthesis of nectrisine, a new immunomodulator isolated from a fungus

The structure of a novel immunomodulator, nectrisine (1), has been elucidated on the basis of chemical and spectroscopic evidence. Its absolute stereochemistry was predicted on the basis of the dibenzoate chirality rule and finally confirmed by a synthesi