202344-79-4

Basic information

• Product Name: (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone
• Synonyms: (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone
• CAS NO: 202344-79-4
• Molecular Weight: 357.493
• Mol File: 202344-79-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone(202344-79-4)
• EPA Substance Registry System: (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone(202344-79-4)

Safety Data

• Hazardous Substances Data: 202344-79-4(Hazardous Substances Data)

Upstream product

• 70-07-5 mephenoxalone 
• 106-95-6 allyl bromide 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 
• 202344-78-3 (S)-4-phenylmethyl-3-(1'-oxononanoyl)-2-oxazolidinone 

Downstream Products

• 202345-17-3 (2R)-2-(2-Oxo-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide 

Relevant articles and documents

Total synthesis and absolute configuration of minalemine A, a guanidine peptide from the marine tunicate Didemnum rodriguesi

The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the β-amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical 1H NMR and very similar 13C NMR spectra compared to the two synthetic diastereomers. Sufficient differences in their chromatographic behavior to allow conclusive identification were not found. However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent β-amino diacid, Ncma.

Mercaptoketones and mercaptoalcohols, a process for their preparation and their use as inhibitors of matrix metalloproteinases

This invention relates to matrix metalloproteinase (MMP) inhibiting compounds of the formula: where R1is C1-C12alkyl, straight or branched and optionally substituted by halogen, hydroxy, C1-C6alkoxy, amino, carboxyl, C1-C6alkoxycarbonyl, carboxamido, nitrile, mono- or di-(C1-C6)alkylamino, thio, C1-C6alkylthio, aryl, -Oaryl or -OCH2aryl where aryl is optionally substituted with C1-C6alkyl, C1-C6alkoxy, carboxy, halogen, cyano, nitro, carboxamido, or hydroxy; and C1-C6alkanesulfonyloxy. R2is α-OH or β-OH and R6is H or R2and R6together are carbonyl; the chemical intermediates; and processes for the preparation of these compounds and the intermediates thereto. Matrix metalloproteinases (MMP) are a family of zinc-containing calcium dependent proteinases, including stromelysins, collagenases, and gelatinases. These MMP enzymes are capable of degrading the proteinaceous components of connective tissue and appear to be involved in tissue remodeling, i.e., wound healing and connective tissue turnover. Unexpectedly, the mercaptoalcohols with the S-configuration at the hydroxyl-bearing carbon have been found to be at least 4 times more potent than the analogous (R)-alcohols both in vitroand in vivoin inhibiting the MMP enzyme..