(2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester

Base Information

• Chemical Name: (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester
• CAS No.: 1235712-37-4
• Molecular Formula: C₂₁H₃₁N₃O₅S
• Molecular Weight: 437.56
• Mol file: 1235712-37-4.mol

Synonyms:(2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester

Chemical Property of (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester

There total 4 articles about (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-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:

N4-propionyl cytosine (21261-08-5) + (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate (1144099-18-2,147126-67-8) → (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester (1235712-37-4)

Guidance literature:

N₄-propionyl cytosine; With methanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In toluene; at 20 - 113 ℃;

(1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate; With triphenylmethyl perchlorate; In dichloromethane; toluene; at 10 - 56 ℃; Inert atmosphere;

Reference yield:

N4-propionyl cytosine (21261-08-5) + (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate (1144099-18-2,147126-67-8) → (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester (1235712-37-4) + C21H31N3O5S

Guidance literature:

N₄-propionyl cytosine; With methanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In toluene; at 20 - 113 ℃;

(1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate; With triphenylmethyl perchlorate; In dichloromethane; toluene; at 10 - 55 ℃; Product distribution / selectivity; Inert atmosphere;

Reference yield:

(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3) → (2R,5S)-5-(N-4-propionylcytosin-1-yl)-1,3-oxathiolane-2R-carboxylic acid (1'R,2'S,5'R)-menthyl ester (1235712-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / dmap / di-isopropyl ether / 5 - 20 °C

2.1: 1,1,1,3,3,3-hexamethyl-disilazane / methanesulfonic acid / toluene / 4 h / Reflux

2.2: 15 - 57 °C

With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane; dmap; methanesulfonic acid; In di-isopropyl ether; toluene;

upstream raw materials:

N₄-propionyl cytosine

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

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

Downstream raw materials:

lamivudine

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

Refernces

• 1、 -. "IMPROVED PROCESS FOR NUCLEOSIDES". Page/Page column 12-13. . Retrieved 2011/08/03.