Adenosine, 2-chloro-N-methyl-2',3'-O-(1-methylethylidene)-4'-thio-, 5'-benzoate

Base Information

• Chemical Name: Adenosine, 2-chloro-N-methyl-2',3'-O-(1-methylethylidene)-4'-thio-, 5'-benzoate
• CAS No.: 596103-12-7
• Molecular Formula: C21H22ClN5O4S
• Molecular Weight: 475.956
• Mol file: 596103-12-7.mol

Synonyms:benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl-methyl ester;Benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester;

Chemical Property of Adenosine, 2-chloro-N-methyl-2',3'-O-(1-methylethylidene)-4'-thio-, 5'-benzoate

Chemical Property:

• Boiling Point: 618.9±65.0 °C(Predicted)
• PSA: 125.69000
• Density: 1.58±0.1 g/cm3(Predicted)
• LogP: 3.58550

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Adenosine, 2-chloro-N-methyl-2',3'-O-(1-methylethylidene)-4'-thio-, 5'-benzoate

There total 15 articles about Adenosine, 2-chloro-N-methyl-2',3'-O-(1-methylethylidene)-4'-thio-, 5'-benzoate 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: 85.0%

methylamine (74-89-5) + benzoic acid (3aS,4R,6R,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-10-5) → benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-12-7)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 24h; Product distribution / selectivity;

Reference yield: 80.0%

benzoyl chloride (98-88-4) + [(3aS,4R,6R,6aR)-6-(2-Chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl]-methanol (596103-17-2) → benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-12-7)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1021/jm034098e

Reference yield: 70.0%

methylamine (74-89-5) + benzoic acid (3aS,4R,6R,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-10-5) → [(3aS,4R,6R,6aR)-6-(2-Chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl]-methanol (596103-17-2) + benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-12-7)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jm034098e

upstream raw materials:

benzoyl chloride

[(3aS,4R,6R,6aR)-6-(2-Chloro-6-methylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl]-methanol

methylamine

benzoic acid (3aS,4R,6R,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

Downstream raw materials:

Benzoic acid (2R,3S,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2-chloro-6-methylamino-purin-9-yl)-tetrahydro-thiophen-2-ylmethyl ester

benzoic acid (2R,3S,4R,5R)-5-[2-chloro-6-methylaminopurin-9-yl]-3,4-dihydroxy-tetrahydro-thiophen-2-ylmethyl ester