147027-10-9

Basic information

• Product Name: (1R,2S,5R)-Menthyl-(2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid
• Synonyms: (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathio;Menthyl-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid;(2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxat;(1R,2S,5R)-Menthyl-(2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid;(1R,2S,5R)-MENTHYL-(2R,5S)-5-(4-AMINO-2-OXO-2H-5-FLUORO-PYRIMIDIN-1-YL)-[1,3]-OXATHIOLANE-2-CARBOXYLIC ACID;(1'R,2'S,5'R)-Menthyl-(2R,5S)-5-(4-Amino-2-Oxo-2H-Pyrimidin-1-yl)-[1,3]Oxathiolane-2-Caboxylicacid;(2R-CIS)-5-(4-AMINO-1,2-DIHYDRO-2-OXO-1-PYRIMIDINYL);(2R-CIS)-5-(4-AMINO-1,2-DIHYDRO-2-OXO-1-PYRIMIDINYL) (CME)
• CAS NO: 147027-10-9
• Molecular Formula: C₁₈H₂₇N₃O₄S
• Molecular Weight: 381.48968
• EINECS: 1308068-626-2
• Product Categories: chiral;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 147027-10-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 203-210°C
• Boiling Point: 524.954 °C at 760 mmHg
• Flash Point: 271.283 °C
• Appearance: tan solid
• Density: 1.421 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: -20°C Freezer
• PKA: 4.18±0.10(Predicted)
• CAS DataBase Reference: (1R,2S,5R)-Menthyl-(2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-Menthyl-(2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid(147027-10-9)
• EPA Substance Registry System: (1R,2S,5R)-Menthyl-(2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid(147027-10-9)

Safety Data

• Hazardous Substances Data: 147027-10-9(Hazardous Substances Data)

Usage

Chemical Properties

Tan Solid

Uses

Different sources of media describe the Uses of 147027-10-9 differently. You can refer to the following data:
1. Lamivudine intermediate.
2. A Lamivudine (L172500) intermediate.

InChI:InChI=1/C18H27N3O4S/c1-10(2)12-5-4-11(3)8-13(12)24-16(22)17-25-15(9-26-17)21-7-6-14(19)20-18(21)23/h6-7,10-13,15,17H,4-5,8-9H2,1-3H3,(H2,19,20,23)/t11-,12+,13-,15+,17-/m1/s1

Upstream product

• 74441-18-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-mercaptoacetate 
• 200396-19-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate 
• 26315-61-7 L-menthyl glyoxylate 
• 21758-30-5 (1R,2S,5R)-(-)-menthyl dichloroacetate 
• 2216-51-5 (-)-menthol 
• 18037-10-0 2,4-O,N-bis(trimethylsilyl)cytosine 
• 147027-09-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 71-30-7 Cytosine 
• 288325-76-8 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester 
• 111969-64-3 L-menthyl glyoxylate monohydrate 
• 1039400-12-8 (2R,5S)-5-(cytosin-1-yl)-1,3-oxathiolane-2-carboxylic acid (1'R,2'S,5'R)-menthyl ester methanesulfonic acid sakt 
• 1309459-32-2 5-hydroxy-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methylcyclohexyl ester 
• 1321928-66-8 5-(pyridin-2-yloxy)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester 
• 1321928-67-9 5-(pyridin-2-ylsulfanyl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester 

Downstream Products

• 173522-96-8 lamivudine salicyclic acid salt 
• 134678-17-4 lamivudine 
• 1321928-69-1 4-amino-1-((2R,5S)-2-hydroxymethyl-[1,3]oxothiolane-5-yl)-1H-pyrimidin-3-one 2-fluorobenzoic acid salt 
• 2216-51-5 (-)-menthol 

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.

Synthetic method for lamivudine

The invention provides a synthetic method for lamivudine. The synthetic method comprises the following steps: cheap easily-available dihaloacetic acid is used as a raw material, the dihaloacetic acidand L-menthol are subjected to condensation, hydrolysis is performed to obtain menthyl glyoxylate, the menthyl glyoxylate and 2,5-dihydroxy-1,4-dithiane are subjected to condensation, halogenation isperformed, the halogenated product and silanized cytosine are subjected to coupling, reduction is performed, the reduced product and salicylic acid are subjected to salt formation to obtain the a salicylate, and finally recrystallization is performed to obtain the optically-pure lamivudine. According to the method provided by the invention, the raw materials used in the whole synthetic process arecheap and easy to obtain, the synthetic process is simple, the synthetic conditions are mild, so that the synthetic costs of the lamivudine are greatly reduced; the raw material utilization rate andreaction selectivity are high, so that the yield of the obtained lamivudine is higher; and at the same time, a chiral substrate is easily removed during the synthesis, three waste (waste water, wastegas and solid waste) generated in the method are less, and the method is suitable for industrialized large-scale production of the lamivudine.

PROCESS FOR PRODUCING LAMIVUDINE AND EMTRICITABINE

This invention provides for flow and batch synthesis processes for the production of Lamivudine and Emtricitabine, including flow and batch synthesis processes wherein at least of the synthesis steps are conducted in a solvent free environment.