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

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

Uses

Used in Pharmaceutical Industry:
(2R,5R)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate is used as a key intermediate in the synthesis of [application type] for [application reason] the production of Lamivudine and Emtricitabine, which are important antiviral medications used in the treatment of HIV and hepatitis B. Its role in the synthesis process is crucial for the development of these life-saving drugs.
Chemical Properties:
The compound is characterized as a white solid, which is a common physical state for many organic compounds used in the pharmaceutical industry. Its specific chemical properties contribute to its reactivity and utility in the synthesis of the target medications.

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

• 2216-51-5 (-)-menthol 
• 108-24-7 acetic anhydride 
• 147126-62-3 (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester 
• 1309459-32-2 5-hydroxy-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methylcyclohexyl ester 
• 147126-67-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate 
• 200396-19-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate 
• 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 
• 1214906-07-6 (-)-menthol 

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 
• 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 
• 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 
• 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 
• 389128-28-3 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester 
• 160579-73-7 (1'R,2'S,5'R)-menthyl-1,3-oxathiolan-2R-carboxylate 

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)

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.

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.

COMBINED TREATMENT WITH A TLR7 AGONIST AND AN HBV CAPSID ASSEMBLY INHIBITOR

The present invention is directed to compositions and methods for treating hepatitis B virus infection. In particular, the present invention is directed to a combination therapy comprising administration of a TLR7 agonist and an HBV capsid assembly inhibi

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.

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.

PROCESS FOR PREPARATION OF CIS-NUCLEOSIDE DERIVATIVE

The present invention relates to a novel and stereoselective synthetic process for the preparation of optically active cis-nucleoside derivatives of compound of Formula (I), wherein R3 represents H, F, Cl, C1-16 alkyl.

PROCESS FOR THE PREPARATION OF CIS-NUCLEOSIDE DERIVATIVE

The present invention relates to a novel and stereoselective synthetic process for the preparation of optically active cis-nucleoside derivatives of compound of Formula (I), wherein R3 represents H, F, Cl, C1-16 alkyl.

Practical enantioselective synthesis of lamivudine (3TC) via a dynamic kinetic resolution

A practical enantioselective synthesis of lamivudine 1 is described. A highly effective dynamic kinetic resolution of the 5-hydroxyoxathiolane, followed by chlorination and introduction of cytosine provides an efficient synthesis of lamivudine.