200396-19-6

Basic information

• Product Name: (1r,2s,5r)-2-Isopropyl-5-Methylcyclohexyl-5-Hydroxy-1,3oxathiolane-2-Carboxylate
• Synonyms: (1r,2s,5r)-2-Isopropyl-5-Methylcyclohexyl-5-Hydroxy-1,3oxathiolane-2-Carboxylate
• CAS NO: 200396-19-6
• Molecular Formula: C₁₄H₂₄O₄S
• Molecular Weight: 287.39502
• Mol File: 200396-19-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 402.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.84±0.40(Predicted)
• CAS DataBase Reference: (1r,2s,5r)-2-Isopropyl-5-Methylcyclohexyl-5-Hydroxy-1,3oxathiolane-2-Carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1r,2s,5r)-2-Isopropyl-5-Methylcyclohexyl-5-Hydroxy-1,3oxathiolane-2-Carboxylate(200396-19-6)
• EPA Substance Registry System: (1r,2s,5r)-2-Isopropyl-5-Methylcyclohexyl-5-Hydroxy-1,3oxathiolane-2-Carboxylate(200396-19-6)

Safety Data

• Hazardous Substances Data: 200396-19-6(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 74441-18-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-mercaptoacetate 
• 40018-26-6 1,4-dithiane-2,5-diol 
• 111969-64-3 L-menthyl glyoxylate monohydrate 

Downstream Products

• 1346921-53-6 L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate 
• 1346921-70-7 C₁₄H₂₃ClO₃S 
• 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 
• 147126-67-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate 
• 147126-65-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 147126-67-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2S,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 147027-09-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 147126-67-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2S,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 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 
• 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 
• 147126-73-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate 

Relevant articles and documents

Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation

A new route was developed for construction of the oxathiolane intermediate used in the synthesis of lamivudine (3TC) and emtricitabine (FTC). We developed the presented route by constraining ourselves to low-cost, widely available starting materials - we refer to this as supply-centered synthesis. Sulfenyl chloride chemistry was used to construct the framework for the oxathiolane from acyclic precursors. This bond construction choice enabled the use of chloroacetic acid, vinyl acetate, sodium thiosulfate, and water to produce the oxathiolane.

Semi-continuous multi-step synthesis of lamivudine

We report the first continuous flow synthesis of lamivudine, an antiretroviral drug used in the treatment of HIV/AIDS and hepatitis B. The key intermediate (5-acetoxy oxathiolane) was prepared by an integrated two step continuous flow process from l-menthyl glyoxalate hydrate in a single solvent, in 95% overall conversion. For the crucial glycosidation reaction, using pyridinium triflate as the novel catalyst, an improved conversion of 95% was obtained. The overall isolated yield of the desired isomer of lamivudine (40%) was improved in the flow synthesis compared to the batch process.

AN IMPROVED PROCESS FOR THE MANUFACTURE OF LAMIVUDINE

The present invention relates to an improved process for the Manufacture of Lamivudine. A process for the preparation of essentially enantiomerically pure (-)-[2R, 5S]-4-amino-1-[2- (hydroxymethyl)-1,3-oxathiolan-5-y1]-2(1H)-pyrimidin-2-one of formula (I), from L-menthyl glyoxylate is described. Also provided is a process for preparation of (+)-1- (2R/S-Cis)-4-amino-1-[(2-hydroxymethyl)-1,3-oxathiolan-5-y1]-2(1H)-pyrimidin-2-one of formula (XII), from L-menthyl glyoxylate.