147027-09-6

Basic information

• Product Name: (2R,5R)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate
• Synonyms: (2R,5R)-5-(Acetyloxy)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl -2-(1-methylethyl)cyclohexyl Ester;(2R,5R)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;(2R,5R)-L-Methyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;(2R,5R)-;(2R,5R)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;(2R,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
• CAS NO: 147027-09-6
• Molecular Formula: C₁₆H₂₆O₅S
• Molecular Weight: 330.44
• Product Categories: Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds;Chiral Reagents, Heterocycles, Sulfur & Selenium Compounds
• Mol File: 147027-09-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 97-99°C
• Boiling Point: 412.459°C at 760 mmHg
• Flash Point: 190.406°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: (2R,5R)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate(147027-09-6)
• EPA Substance Registry System: (2R,5R)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate(147027-09-6)

Safety Data

• Hazardous Substances Data: 147027-09-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An intermediate for the preparation of Lamivudine and Emtricitabine.

InChI:InChI=1/C16H26O5S/c1-9(2)12-6-5-10(3)7-13(12)20-15(18)16-21-14(8-22-16)19-11(4)17/h9-10,12-14,16H,5-8H2,1-4H3/t10-,12+,13-,14-,16-/m1/s1

Upstream product

• 1214906-07-6 (-)-menthol 
• 147126-67-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate 
• 1309459-32-2 5-hydroxy-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methylcyclohexyl ester 
• 108-24-7 acetic anhydride 
• 2216-51-5 (-)-menthol 
• 200396-19-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate 
• 147126-62-3 (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester 
• 111969-64-3 L-menthyl glyoxylate monohydrate 
• 147027-43-8 (2R,5R)-5-Acetoxy-[1,3]oxathiolane-2-carboxylic acid 
• 440105-45-3 TRANS-5-ACETOXY-1,3-OXATHIOLANE-2-CARBOXYLIC-ACID 

Downstream Products

• 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 
• 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 
• 147126-73-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate 
• 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 
• 764659-79-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate 
• 160579-73-7 (1'R,2'S,5'R)-menthyl-1,3-oxathiolan-2R-carboxylate 
• 389128-28-3 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester 

Relevant articles and documents

Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation

By simple combination of water and sodium iodide (NaI) with chlorotrimethylsilane (TMSCl), promotion of a Vorbrüggen glycosylation en route to essential HIV drugs emtricitabine (FTC) and lamivudine (3TC) is achieved. TMSCl-NaI in wet solvent (0.1 M water)

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.

Highly stereoselective synthesis of lamivudine (3TC) and emtricitabine (FTC) by a novel N -glycosidation procedure

The combined use of silanes (Et3SiH or PMHS) and I2 as novel N-glycosidation reagents for the synthesis of bioactive oxathiolane nucleosides 3TC and FTC is reported. Both systems (working as anhydrous HI sources) were devised to act as substrate activators and N-glycosidation promoters. Excellent results in terms of chemical efficiency and stereoselectivity of the reactions were obtained; surprisingly, the nature of the protective group at the N4 position of (fluoro)cytosine additionally influenced the stereochemical reaction outcome.