112663-80-6

Basic information

• Product Name: (S)-2-oxazolidinone-5-carboxylic acid benzyl ester
• Synonyms: (S)-2-oxazolidinone-5-carboxylic acid benzyl ester
• CAS NO: 112663-80-6
• Molecular Weight: 221.213
• Mol File: 112663-80-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-2-oxazolidinone-5-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-oxazolidinone-5-carboxylic acid benzyl ester(112663-80-6)
• EPA Substance Registry System: (S)-2-oxazolidinone-5-carboxylic acid benzyl ester(112663-80-6)

Safety Data

• Hazardous Substances Data: 112663-80-6(Hazardous Substances Data)

Usage

General Description

"(S)-2-oxazolidinone-5-carboxylic acid benzyl ester" is a chemical compound with a molecular formula of C11H11NO4. It is a benzyl ester of (S)-2-oxazolidinone-5-carboxylic acid, which is a versatile intermediate in the synthesis of pharmaceutical compounds. The benzyl ester group is derived from benzyl alcohol and is commonly used as a protecting group in organic synthesis. (S)-2-oxazolidinone-5-carboxylic acid benzyl ester is often employed in the preparation of various pharmaceuticals and can also be used as a building block in the synthesis of other organic compounds. Its versatile nature and utility in chemical synthesis make it a valuable compound in the pharmaceutical and chemical industries.

Upstream product

• 66178-04-9 (S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid 

Downstream Products

• 169688-48-6 benzyl-(S)-N-tert-butoxycarbonyl-2-oxo-5-oxazolidine carboxylate 
• 7517-99-9 (S)-5-(hydroxymethyl)-1,3-oxazolidin-2-one 

Relevant articles and documents

Design and synthesis of sulfur based inhibitors of matrix metalloproteinase-1.

Fibroblast collagenase (MMP-1), a member of the matrix metalloproteinases family, is believed to be a pathogenesis of arthritis, by cleaving triple-helical type II collagen in cartilage. From the similarity of the active site zinc binding mode with hydroxamate, we designed and synthesized alpha-mercaptocarbonyl possessing compounds (3-5), which incorporated various peptide sequences as enzyme recognition sites. The P4-P1 peptide incorporating compound (3) exhibited as potent inhibition as the hydroxamate (1) and the carboxylate (2) type inhibitors, with an IC50 of 10(-6) M order against MMP-1. But the inhibitor (3) related compounds (6-8) displayed decreased or no inhibitory potencies. These results suggest that the existence of both the carbonyl and thiol groups might be critical for the inhibition, and the distance between the two functional groups is important for inhibitory potency. For Pn' peptide incorporating compounds (4a-k), except for 4h and 4k, all compounds showed IC50 values under sub-nanomolar. Among them, for potent inhibition, Leu was better than Phe and Val as the P1' amino acid, and the P2' position amino acid was necessary, and preferentially Phe. Insertion of the Pn peptide into 4d or 4k, giving compounds 5a-c, did not increase the activities of 4d and 4k. Substitution of the mercapto group with other functional groups lost the activity of compound 4a. The stereochemical preference at the thiol-attached position was also determined by preparation of both isomers of 4a. It was found that the S configuration compound (36b) is approximately 100 times more potent than the corresponding R-isomer (36a).

A facile synthesis of (S)-isoserine from (S)-malic acid

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Efficient Pathways to (R)- and (S)-5-Hydroxymethyl-2-oxazolidinone and some Derivatives

2-Oxazolidinones are a very interesting class of compounds due to their various pharmacological effects.Two new syntheses of enantiomerically pure (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been developed starting with D-mannitol, L-ascorbic acid and (R)- or (S)-malic acid. (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been used to synthesize some new homochiral 2-oxazolidinone derivatives.