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

Base Information

• Chemical Name: 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester
• CAS No.: 288325-76-8
• Molecular Formula: C₁₄H₂₃ClO₃S
• Molecular Weight: 306.854
• Mol file: 288325-76-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-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: 93.5%

(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3) → 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester (288325-76-8)

Guidance literature:

With hydrogenchloride; C₃₃H₃₄N₅O⁽¹⁺⁾*Cl^(1-); zinc(II) chloride; In dichloromethane; water; at 20 ℃; Concentration; stereoselective reaction;

Reference yield:

5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester → 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester (288325-76-8)

Guidance literature:

5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester; With methanesulfonic acid; In dichloromethane; N,N-dimethyl-formamide; at 25 ℃; for 0.5h;

With thionyl chloride; at 5 - 15 ℃; for 2.5h;

Reference yield:

L-menthyl glyoxylate monohydrate (111969-64-3) → 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester (288325-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene

1.2: 80 percent / Et₃N / toluene; hexane

2.1: SOCl₂ / dimethylformamide; CH₂Cl₂

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2005.10.002

upstream raw materials:

(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester

L-menthyl glyoxylate monohydrate

Downstream raw materials:

(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

(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

Refernces

• 1、 -. "Preparation method for nucleoside analogue". Paragraph 0024; 0025; 0027; 0028; 0029; 0030. . Retrieved 2017/01/02.
• 2、 Goodyear, Michael D.,Hill, Malcolm L.,West, Jono P.,Whitehead, Andrew J.. "Practical enantioselective synthesis of lamivudine (3TC) via a dynamic kinetic resolution". . p. 8535 - 8538. Retrieved 2007/10/03.