1012053-56-3

Basic information

• Product Name: (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester
• Synonyms: (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester
• CAS NO: 1012053-56-3
• Molecular Weight: 411.522
• Mol File: 1012053-56-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester(1012053-56-3)
• EPA Substance Registry System: (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester(1012053-56-3)

Safety Data

• Hazardous Substances Data: 1012053-56-3(Hazardous Substances Data)

Upstream product

• 1091585-23-7 C₁₅H₂₅ClO₄S 
• 18037-10-0 2,4-O,N-bis(trimethylsilyl)cytosine 
• 71-30-7 Cytosine 
• 1012053-49-4 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2-oxoethyl) carbonate 
• 14602-86-9 (1R,2S,5R)-menthyl chloroformate 
• 2216-51-5 (-)-menthol 

Downstream Products

• 134678-17-4 lamivudine 

Relevant articles and documents

Asymmetric preparation method of lamivudine

The invention provides an asymmetric preparation method of lamivudine. The preparation method comprises the steps: reacting L-menthyl chloroformate serving as a raw material with 2-halogenated ethanol, and carrying out oxidation to obtain menthol acetaldehyde, condensing menthol acetaldehyde with 2,5-dihydroxy-1,4-dithiane under the asymmetric induction of optically active alcohol to generate trans-5-hydroxy-1,3-oxythioheterocyclopentane-2-methylmenthol ester, acetylating the intermediate, then, coupling the acetated product to silanized cytosine, next, carrying out hydrolysis, then, forming asalt by using a hydrolyzed product and salicylic acid, and finally, carrying out recrystallization to obtain optically pure lamivudine. The raw materials used in the whole synthesis process are cheap, available and high in utilization ratio, so that the synthesis cost of lamivudine provided by the invention is greatly reduced; moreover, the synthesis process is simple, the synthesis condition ismild, and the yield of the obtained lamivudine is relatively high; and meanwhile, a chiral substrate is easy to remove in a synthesis process, few wastewater, waste gas and waste residue pollutants are generated, and the asymmetric preparation method is suitable for large-scale industrial production of lamivudine.

A preparation method of lamivudine

The invention discloses a method for preparation of lamivudine. Refined pure 5 S - (cytosine base - 1 ') - 1, 3 - oxathiolane - 2 - ethoxy carbonyl - (1' R, 2'S, 3' R) - menthyl ester; in the weak base and the solvent removed under the condition of chiral L - menthol to get a product of lamivudine. The material of the invention is cheap, the reagents used in the environmental protection, steps is relatively short, mild reaction conditions, atom utilization rate high, high yield, high chemical purity of the obtained product, reach the medical standard, suitable for large-scale production of lamivudine preparation method.