(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl (2R,5R)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate

Base Information

• Chemical Name: (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl (2R,5R)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate
• CAS No.: 147027-09-6
• Molecular Formula: C16H26 O5 S
• Molecular Weight: 330.445
• DSSTox Substance ID: DTXSID50433940
• Nikkaji Number: J650.872C
• Wikidata: Q82248216
• Mol file: 147027-09-6.mol

Synonyms:147027-09-6;(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl (2R,5R)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;(2R,5R)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate;[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R,5R)-5-acetyloxy-1,3-oxathiolane-2-carboxylate;1,3-Oxathiolane-2-carboxylic acid, 5-(acetyloxy)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2R,5R)-;(2R,5R)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;SCHEMBL12635116;DTXSID50433940;JYUPOLQFLIRYEQ-PBEGBBSFSA-N;AKOS025294536;AS-75011;CS-0357098;(2R,5R)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl5-acetoxy-1,3-oxathiolane-2-carboxylate;(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-acetoxy-1,3-oxathiolane-2-carboxylate;(2R)-5alpha-Acetoxy-1,3-oxathiolane-2beta-carboxylic acid (1R,3R,4S)-p-menthan-3beta-yl ester

Chemical Property of (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl (2R,5R)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 97-99°C
• Refractive Index: 1.511
• Boiling Point: 412.459°C at 760 mmHg
• Flash Point: 190.406°C
• PSA: 87.13000
• Density: 1.16g/cm³
• LogP: 2.96910
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Methanol
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 330.15009510
• Heavy Atom Count: 22
• Complexity: 411

Purity/Quality:

100% ^*data from raw suppliers

(2R,5R)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)C2OC(CS2)OC(=O)C)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)[C@@H]2O[C@H](CS2)OC(=O)C)C(C)C
• Uses: An intermediate for the preparation of Lamivudine and Emtricitabine.

Technology Process of (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl (2R,5R)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate

There total 13 articles about (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl (2R,5R)-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate 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: 80.0%

Acetic acid (2R,5R)-2-chlorocarbonyl-[1,3]oxathiolan-5-yl ester + (-)-menthol (1214906-07-6) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8)

Guidance literature:

With pyridine;

DOI:10.1016/j.tetlet.2005.10.002

Reference yield: 48.24%

acetic anhydride (108-24-7) + (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8)

Guidance literature:

acetic anhydride; (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester; With pyridine; In dichloromethane; acetone; at 20 ℃;

With triethylamine; In hexane; acetone; at -10 ℃; for 24h; Solvent; Reagent/catalyst; Temperature;

Reference yield: 48.0%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate (147126-67-8) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8)

Guidance literature:

With triethylamine; In hexane; at -20 ℃; for 36h;

DOI:10.1039/c7ob00480j

upstream raw materials:

(-)-menthol

(-)-menthol

TRANS-5-ACETOXY-1,3-OXATHIOLANE-2-CARBOXYLIC-ACID

(2R,5R)-5-Acetoxy-[1,3]oxathiolane-2-carboxylic acid

Downstream raw materials:

(1'R,2'S,5'R)-menthyl-1,3-oxathiolan-2R-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate

(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