(3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

Base Information

• Chemical Name: (3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide
• CAS No.: 1053243-75-6
• Molecular Formula: C₂₁H₂₃BrN₆O₄
• Molecular Weight: 503.355
• Mol file: 1053243-75-6.mol

Synonyms:(3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

Chemical Property of (3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

There total 3 articles about (3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 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:

4-bromobenzylamine hydrochloride (26177-44-6) + 2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide (152918-47-3) → (3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide (1053243-75-6)

Guidance literature:

With triethylamine; In ethanol; at 75 ℃; for 16h;

DOI:10.1021/jm00031a014

Reference yield:

1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride (104940-65-0) → (3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide (1053243-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CHCl₃ / 0.25 h / 10 °C

2: Et₃N / ethanol / 16 h / 75 °C

With triethylamine; In ethanol; chloroform;

DOI:10.1021/jm00031a014

Reference yield:

2',3'-isopropylideneinosine-5'-carboxylic acid → (3aS,4S,6R,6aR)-6-[6-(4-Bromo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide (1053243-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / dimethylformamide; CHCl₃ / 6 h / Heating

2: CHCl₃ / 0.25 h / 10 °C

3: Et₃N / ethanol / 16 h / 75 °C

With thionyl chloride; triethylamine; In ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm00031a014

upstream raw materials:

4-bromobenzylamine hydrochloride

2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide

1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride