112663-80-6

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-oxazolidinone-5-carboxylic acid benzyl ester is used as a versatile intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-oxazolidinone-5-carboxylic acid benzyl ester is used as a building block for the creation of other organic compounds. Its benzyl ester group provides a convenient protecting group, which can be selectively removed when needed, allowing for the synthesis of complex organic molecules.
Used in Chemical Industry:
(S)-2-oxazolidinone-5-carboxylic acid benzyl ester is also utilized in the chemical industry for the production of various chemical products. Its ability to act as a versatile intermediate makes it a valuable compound for the synthesis of a wide range of chemical substances.

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 academic research and scientific papers

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).

Efficient synthesis of N-benzyloxycarbonyl- and N-tert-butoxycarbonyl-(S)-isoserine and their derivatives

A mild and efficient synthesis of N-protected (S)-isoserine from (S)-malic acid monoester via an oxazolidin-2-one is described.

A concise synthesis of (R)-GABOB from L-malic acid

A concise synthesis of (R)-4-amino-3-hydroxybutanoic acid, starting from L-malic acid, is reported. The approach is based on the conversion of the oxazolidin-2-one 9 into a full protected form of (R)-GABOB by an Anrdt-Eistert reaction.

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.