(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

Base Information

• Chemical Name: (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• CAS No.: 764659-72-5
• Molecular Formula: C18H26FN3O4S
• Molecular Weight: 399.487
• Mol file: 764659-72-5.mol

Synonyms:(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester; emtricitabine intermediate FCME

Chemical Property of (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

Chemical Property:

• Boiling Point: 508.5±60.0 °C(Predicted)
• PKA: 2.40±0.10(Predicted)
• PSA: 122.73000
• Density: 1.47
• LogP: 2.89910
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Sparingly, Heated), Methanol (Slightly, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylicAcid(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester is an intermediate in the synthesis of Emtricitabine (E525000). A reverse transcriptase inhibitor. It is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner. A nucleoside analog structurally related to Lamivudine (L172500).

Technology Process of (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

There total 26 articles about (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.7%

C21H31FN4O4S → (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 (764659-72-5,764659-79-2)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 20 - 25 ℃;

Reference yield: 91.0%

Flucytosine (2022-85-7) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8) → (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 (764659-72-5,764659-79-2)

Guidance literature:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate; With triethylsilane; iodine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

Flucytosine; With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 0 - 20 ℃; for 1h; Reagent/catalyst; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00982

Reference yield: 81.0%

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine (111878-21-8) + 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester (288325-76-8) → (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 (764659-72-5,764659-79-2)

Guidance literature:

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine; 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester; With triethylamine; In dichloromethane; at 42 - 45 ℃; for 19h; Heating / reflux;

With water; at 25 ℃; for 0.5h;

upstream raw materials:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine

5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester

Flucytosine

Downstream raw materials:

emtricitabine

4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt

Refernces

• 1、 -. "Emtricitabine synthesis method". Paragraph 0028; 0034; 0038. . Retrieved 2019/11/29.
• 2、 -. "Preparation method for emtricitabine hydrohalide". Paragraph 0048; 0049; 0050. . Retrieved 2017/08/27.