147126-62-3

Basic information

• Product Name: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• Synonyms: (2R,5R)-5-Hydroxy-[1,3]-oxathiolane-2-carboxylic acid menthyl ester (HME);(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylate;(2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester;(2R, 5R)-5-HYDROXY-1,3-OXATHIOLANE-2-CARBOXYLIC ACID METHYL ESTER;[1R-[1a(2R*,5R*),2b,5a]]-5-Hydroxy-1,3-Oxathiolane-2-carboxylic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester;(2S,5R)-5-Hydroxy-[1,3]-oxathiolane-2-carboxylic acid menthyl ester (HME);(2R, 5R)-5-HYDROXY-1,3-OXATHIOLANE-2-CARBOXYLIC ACID L METHYL ESTER;(2S,5R)-5-Hydroxy-[1,3]-oxathiolane-2-carboxylic acid menthyl ester
• CAS NO: 147126-62-3
• Molecular Formula: C₁₄H₂₄O₄S
• Molecular Weight: 288.4
• EINECS: 1806241-263-5
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 147126-62-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 99-1010C
• Boiling Point: 402.3 °C at 760 mmHg
• Flash Point: 197.1 °C
• Appearance: /
• Density: 1.16
• Vapor Pressure: 3.53-4.14Pa at 30-50℃
• Refractive Index: 1.527
• Storage Temp.: -20?C Freezer
• PKA: 11.84±0.40(Predicted)
• CAS DataBase Reference: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(147126-62-3)
• EPA Substance Registry System: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(147126-62-3)

Safety Data

• Hazardous Substances Data: 147126-62-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 147126-62-3 differently. You can refer to the following data:
1. (1R,2S,5R)-Methyl-5R-hydroxy-[1,3]-oxathiolane-2R-carboxylate is a useful research chemical compound.
2. Lamivudine (L172500) intermediate.

Chemical Properties

White To Off-White Solid

InChI:InChI=1/C14H24O4S/c1-8(2)10-5-4-9(3)6-11(10)17-13(16)14-18-12(15)7-19-14/h8-12,14-15H,4-7H2,1-3H3/t9-,10+,11?,12-,14-/m1/s1

Upstream product

• 40018-26-6 1,4-dithiane-2,5-diol 
• 111969-64-3 L-menthyl glyoxylate monohydrate 
• 74441-18-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-mercaptoacetate 
• 21758-30-5 (1R,2S,5R)-(-)-menthyl dichloroacetate 
• 2216-51-5 (-)-menthol 
• 26315-61-7 L-menthyl glyoxylate 

Downstream Products

• 288325-76-8 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester 
• 147126-65-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-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 
• 1144099-18-2 (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-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 
• 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 
• 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 
• 1091585-26-0 C₁₅H₂₆O₄S 
• 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 
• 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 
• 528567-31-9 menthyl 5-hydroxy[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.

Emtricitabine synthesis method

The invention provides an emtricitabine synthesis method, which comprises: carrying out condensation on cheap and easily available dihaloacetic acid as a raw material and L-menthol, hydrolyzing to obtain menthyl glyoxylate hydrate, condensing with 2,5-dihydroxy-1,4-dithiane, carrying out halogenation, coupling with silylated 5-flucytosine, reducing, carrying out salt forming with salicylic acid toobtain emtricitabine salicylate, and finally re-crystallizing to obtain optically pure emtricitabine. According to the present invention, the whole synthesis process has characteristics of inexpensive and easily available raw materials, simple synthesis process and mild synthesis conditions, such that the synthesis cost of emtricitabine is substantially reduced; various raw materials have characteristics of good reaction selectivity and high utilization rate, such that the yield of the obtained emtricitabine is high; and the chiral substrate is easily removed during the synthesis, and the generated three-waste pollutants are less, such that the method is suitable for industrial large-scale production of emtricitabine.

A STEREOSELECTIVE PROCESS FOR PREPARATION OF 1,3-OXATHIOLANE NUCLEOSIDES

The present invention relates to a stereoselective glycosylation for the preparation of 1,3-oxathiolane nucleoside in high yield and high optical purity. The invention specifically relates to a process of the preparation of Lamivudine and Emtricitabine using zirconium (IV) chloride (ZrCl4) as a catalyst in glycosylation.