(2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester

Base Information

• Chemical Name: (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester
• CAS No.: 1012053-56-3
• Molecular Formula: C₁₉H₂₉N₃O₅S
• Molecular Weight: 411.522
• Mol file: 1012053-56-3.mol

Synonyms:(2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester

Chemical Property of (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester

There total 10 articles about (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester 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: 73.1%

C15H25ClO4S (1091585-23-7) + Cytosine (71-30-7) → (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester (1012053-56-3)

Guidance literature:

Cytosine; With methanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; Reflux;

C₁₅H₂₅ClO₄S; With triethylamine; In dichloromethane; at 75 ℃; for 7h;

Reference yield: 35.0%

C15H25ClO4S (1091585-23-7) + 2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0) → (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester (1012053-56-3) + C19H29N3O5S

Guidance literature:

2,4-O,N-bis(trimethylsilyl)cytosine; With triethylamine; In dichloromethane; Reflux;

C₁₅H₂₅ClO₄S; In dichloromethane; Reflux;

Reference yield:

[(2R,5R)-5-acetyl-1,3-oxathiolan-2-yl]methyl ((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) carbonate + 2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0) → (2R,5S)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester (1012053-56-3)

Guidance literature:

With triethylamine; In dichloromethane; at 75 ℃; for 7h;

upstream raw materials:

C₁₅H₂₅ClO₄S

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

(-)-menthol

(1R,2S,5R)-menthyl chloroformate

Downstream raw materials:

lamivudine

Refernces

• 1、 -. "Asymmetric preparation method of lamivudine". . . Retrieved 2019/11/21.
• 2、 -. "A PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE". Page/Page column 8-9. . Retrieved 2010/04/24.