5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

Base Information

• Chemical Name: 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester
• CAS No.: 389128-28-3
• Molecular Formula: C₁₈H₂₆N₂O₅S
• Molecular Weight: 382.481
• Mol file: 389128-28-3.mol

Synonyms:5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

Chemical Property of 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

Chemical Property:

Purity/Quality:

NLT 98% ^*data from raw suppliers

(2R,5S)-5-(3,4-Dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylicAcid(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2R,5S)-5-(3,4-Dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl Ester is an intermediate in the synthesis of (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione which is an impurity of Lamivudine (L172500). (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione is also being further studied to determine its potential as an anti-HIV agent.

Technology Process of 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

There total 1 articles about 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl 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:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8) + bis-tert-butyldimethylsilyl-uracil → 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-28-3)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; for 20h;

DOI:10.1016/S0040-4020(01)00800-6

Reference yield: 99.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-28-3) → 5'(S)-[O4-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-29-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(01)00800-6

Reference yield:

5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-28-3) → 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2: 76 percent / CH₂Cl₂ / 0.75 h / 0 °C

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(01)00800-6

upstream raw materials:

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

Downstream raw materials:

5'(S)-[O⁴-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane