(3aS,4S,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

Base Information

• Chemical Name: (3aS,4S,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide
• CAS No.: 152918-48-4
• Molecular Formula: C₂₁H₂₃IN₆O₄
• Molecular Weight: 550.356
• DSSTox Substance ID: DTXSID701106200
• Mol file: 152918-48-4.mol

Synonyms:152918-48-4;(3aS,4S,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide;beta-D-Ribofuranuronamide, 1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-2,3-O-(1-methylethylidene)-;SCHEMBL13382559;DTXSID701106200;(3Ar,4R,6S,6aS)-4-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N,2,2-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide;(3aS,4S,6R,6aR)-6-(6-{[(3-iodophenyl)methyl]amino}-9H-purin-9-yl)-N,2,2-trimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxamide;1-Deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-2,3-O-(1-methylethylidene)-beta-D-ribofuranuronamide

Chemical Property of (3aS,4S,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 550.08255
• Heavy Atom Count: 32
• Complexity: 701

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(O1)C(OC2C(=O)NC)N3C=NC4=C(N=CN=C43)NCC5=CC(=CC=C5)I)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](O1)[C@@H](O[C@@H]2C(=O)NC)N3C=NC4=C(N=CN=C43)NCC5=CC(=CC=C5)I)C

Technology Process of (3aS,4S,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

There total 6 articles about (3aS,4S,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide 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:

2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide (152918-47-3) → IB-MECA acetonide (152918-48-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 70 ℃; for 25h;

Reference yield:

3-iodobenzylamine hydrochloride (3718-88-5) + 2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide (152918-47-3) → IB-MECA acetonide (152918-48-4)

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) → IB-MECA acetonide (152918-48-4)

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

upstream raw materials:

3-iodobenzylamine 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

6-Chloropurine riboside

Downstream raw materials:

N⁶-(3-iodobenzyl)adenosine-5'-N-methyluronamide