5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester

Base Information

• Chemical Name: 5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester
• CAS No.: 147126-73-6
• Molecular Formula: C₁₈H₂₇N₃O₄S
• Molecular Weight: 381.496
• Mol file: 147126-73-6.mol

Synonyms:[1R-[1-A(2S*,5R*),2beta,5beta]]-5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester;

Chemical Property of 5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 4.1E-11mmHg at 25°C
• Melting Point: 99-101 °C
• Refractive Index: 1.654
• Boiling Point: 525 °C at 760 mmHg
• PKA: 4.18±0.10(Predicted)
• Flash Point: 271.3 °C
• PSA: 121.74000
• Density: 1.42 g/cm³
• LogP: 2.99880

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R,2S,5R)-menthyl-5R-hydroxy-[1,3-oxathiolane-2R-carboxylate 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Lamivudine intermediate

Technology Process of 5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester

There total 48 articles about 5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid 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: 95.0%

2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0) + (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-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate (147027-10-9,147126-73-6,147126-74-7,147126-80-5)

Guidance literature:

With pyridinium triflate; In acetonitrile; at 80 ℃; for 0.14h; under 517.162 Torr; Flow reactor;

DOI:10.1039/c7ob00480j

Reference yield: 90.0%

Cytosine (71-30-7) + 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-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate (147027-10-9,147126-73-6,147126-74-7,147126-80-5)

Guidance literature:

With methanesulfonic acid; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; toluene; at 25 - 60 ℃; for 4h; Reflux;

Reference yield: 80.0%

Cytosine (71-30-7) + (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-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate (147027-10-9,147126-73-6,147126-74-7,147126-80-5)

Guidance literature:

Cytosine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 25 - 55 ℃; Inert atmosphere;

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate; With zirconium(IV) chloride; In dichloromethane; at 25 - 30 ℃; for 6h; Reagent/catalyst; Solvent; Concentration; Time; Inert atmosphere;

upstream raw materials:

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

(tert-Butyl-dimethyl-silanyl)-[2-(tert-butyl-dimethyl-silanyloxy)-pyrimidin-4-yl]-amine

2,4-O,N-bis(trimethylsilyl)cytosine

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

Downstream raw materials:

5-(4-amino-2-oxopyrimidine-1(2H)-yl)-1,3-oxathiolane-2-carboxylic acid

Refernces

• 1、 Aher, Umesh P.,Jadhav, Harishchandra S.,Jayashree, B. S.,Shenoy, Gautham G.,Singh, Girij P.,Srivastava, Dhananjai. "Large-Scale Stereoselective Synthesis of 1,3-Oxathiolane Nucleoside, Lamivudine, via ZrCl4-Mediated N-Glycosylation". . p. 387 - 397. Retrieved 2020/04/08.