(2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

Base Information

• Chemical Name: (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• CAS No.: 147126-62-3
• Molecular Formula: C14H24O4S
• Molecular Weight: 288.408
• Mol file: 147126-62-3.mol

Synonyms:(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylate;1,3-Oxathiolane-2-carboxylicacid, 5-hydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, [1R-[1a(2R*,5R*),2b,5a]]-;

Chemical Property of (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

Chemical Property:

• Vapor Pressure: 3.53-4.14Pa at 30-50℃
• Melting Point: 99-1010C
• Refractive Index: 1.527
• Boiling Point: 402.3 °C at 760 mmHg
• PKA: 11.84±0.40(Predicted)
• Flash Point: 197.1 °C
• PSA: 81.06000
• Density: 1.16 g/cm³
• LogP: 2.39830
• Storage Temp.: -20?C Freezer

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1R,2S,5R)-Methyl-5R-hydroxy-[1,3]-oxathiolane-2R-carboxylate is a useful research chemical compound. Lamivudine (L172500) intermediate.

Technology Process of (2R,5R)-5-Hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

There total 8 articles about (2R,5R)-5-Hydroxy-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: 88.0%

1,4-dithiane-2,5-diol (40018-26-6) + L-menthyl glyoxylate monohydrate (111969-64-3) → (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3)

Guidance literature:

With acetic acid; In acetone; at 50 - 125 ℃; Temperature; Solvent;

Reference yield: 86.4%

1,4-dithiane-2,5-diol (40018-26-6) + L-menthyl glyoxylate (26315-61-7) → (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3)

Guidance literature:

L-menthyl glyoxylate; With acetic acid; In toluene; at 100 ℃; Inert atmosphere;

1,4-dithiane-2,5-diol; at 80 ℃; for 2h;

Reference yield:

(-)-menthol (2216-51-5) → (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; dicyclohexyl-carbodiimide / cyclohexane / 8 h / -5 - 100 °C

2.1: tetrabutylammomium bromide / water / 5 h / 95 °C

3.1: acetic acid / toluene / 100 °C / Inert atmosphere

3.2: 2 h / 80 °C

With dmap; tetrabutylammomium bromide; acetic acid; dicyclohexyl-carbodiimide; In cyclohexane; water; toluene;

upstream raw materials:

1,4-dithiane-2,5-diol

L-menthyl glyoxylate monohydrate

L-menthyl glyoxylate

(-)-menthol

Downstream raw materials:

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

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

(1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-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

Refernces

• 1、 -. "Synthetic method for lamivudine". Paragraph 0028; 0032; 0038. . Retrieved 2019/11/21.
• 2、 -. "PROCESS FOR PRODUCING LAMIVUDINE AND EMTRICITABINE". Page/Page column 12; 13; 14; 15; 17; 18. . Retrieved 2018/01/20.