1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide

Base Information

• Chemical Name: 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide
• CAS No.: 152918-47-3
• Molecular Formula: C14 H16 ClN5 O4
• Molecular Weight: 353.765
• DSSTox Substance ID: DTXSID40439431
• Wikidata: Q72458151
• Mol file: 152918-47-3.mol

Synonyms:152918-47-3;1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide;(3aR,4R,6S,6aS)-4-(6-chloropurin-9-yl)-N,2,2-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide;DTXSID40439431;VXKQFHVZIXOPJH-LOKDSWTASA-N;AKOS016011941;A883860;(3aS,4S,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-N,2,2-trimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxamide;(3aS,4S,6R,6aR)-6-(6-Chloro-9H-purin-9-yl)-N,2,2-trimethyltetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxamide (non-preferred name)

Chemical Property of 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide

Chemical Property:

• PSA: 103.88000
• Density: 1.74
• LogP: 1.48350
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 353.0890817
• Heavy Atom Count: 24
• Complexity: 523

Purity/Quality:

97% ^*data from raw suppliers

1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(O1)C(OC2C(=O)NC)N3C=NC4=C3N=CN=C4Cl)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](O1)[C@@H](O[C@@H]2C(=O)NC)N3C=NC4=C3N=CN=C4Cl)C

Technology Process of 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide

There total 7 articles about 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide 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:

(3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (120355-42-2) + methylamine (74-89-5) → 2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide (152918-47-3)

Guidance literature:

(3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid; With thionyl chloride; In acetonitrile; at 30 ℃; for 4h;

methylamine; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile; at 7 ℃; for 13h;

Reference yield:

1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride (104940-65-0) + methylamine (74-89-5) → 2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide (152918-47-3)

Guidance literature:

In chloroform; at 10 ℃; for 0.333333h;

DOI:10.1021/jm00159a020

Reference yield:

2',3'-isopropylideneinosine-5'-carboxylic acid → 2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide (152918-47-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: CHCl₃ / 0.25 h / 10 °C

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

DOI:10.1021/jm00031a014

upstream raw materials:

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

methylamine

2',3'-O-isopropylideneinosine

(3aS,4S,6R,6aR)-2,2-dimethyl-6-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

Downstream raw materials:

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

4-{[9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-ylamino]-methyl}-benzenesulfonic 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

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