1144099-18-2

Basic information

• Product Name: (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate
• Synonyms: (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate
• CAS NO: 1144099-18-2
• Molecular Weight: 330.445
• Mol File: 1144099-18-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate(1144099-18-2)
• EPA Substance Registry System: (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate(1144099-18-2)

Safety Data

• Hazardous Substances Data: 1144099-18-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 147126-62-3 (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester 

Downstream Products

• 147126-78-1 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[4-(methylcarboxamido)-2-oxo-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate 
• 147126-79-2 (2R,5S)-5-(N-4-acetylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester 
• 1235712-37-4 (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester 
• 764659-72-5 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate 
• 147027-10-9 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate 

Relevant articles and documents

IMPROVED PROCESS FOR NUCLEOSIDES

The present invention relates to improved process for the preparation of lamivudine or emtricitabine. Thus, (1'R,2'S,5'R)-menthyl- 5(R,S)-acetoxy-[1,3]-oxathiolane-2(R)-carboxylate is reacted with N-propinoyl cytosine in hexamethyl disilazane and then added trityl perchlorate to obtain a solid containing (1'R,2'S,5'R)-menthyl-5S-(N-4''-propionylcytosin-1''-yl)-[1,3]-oxathiolane -2R-carboxylate. The solid obtained above is reacted with methane sulfonic acid to obtain (2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)- [1,3]-oxathiolane-2-carboxylic acid, 2S-isopropyl-5R-methyl-1R-cyclohexyl ester. The above compound is reduced with sodium borohydride to obtain lamivudine.

PROCESS FOR THE PREPARATION OF CIS-NUCLEOSIDE DERIVATIVE

The present invention relates to a novel and stereoselective synthetic process for the preparation of optically active cis-nucleoside derivatives of compound of Formula (I), wherein R3 represents H, F, Cl, C1-16 alkyl.