I-AB-Meca

Base Information

• Chemical Name: I-AB-Meca
• CAS No.: 152918-27-9
• Molecular Formula: C₁₈H₂₀IN₇O₄
• Molecular Weight: 525.306
• UNII: 9WR19428J3
• DSSTox Substance ID: DTXSID10165159
• Nikkaji Number: J584.726E
• Wikidata: Q27140417
• Pharos Ligand ID: WZ7TL1Q1FG2H
• Metabolomics Workbench ID: 66341
• ChEMBL ID: CHEMBL133566
• Mol file: 152918-27-9.mol

Synonyms:AB-MECA;N(6)-(4-amino-3-iodobenzyl)adenosine-5'-N-methyluronamide

Chemical Property of I-AB-Meca

Chemical Property:

• Refractive Index: 1.842
• PKA: 12.72±0.70(Predicted)
• PSA: 163.93000
• Density: 2.066g/cm³
• LogP: 1.48490
• Storage Temp.: −20°C
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 525.06215
• Heavy Atom Count: 30
• Complexity: 619

Purity/Quality:

98%Min ^*data from raw suppliers

I-AB-MECA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=C(C=C4)N)I)O)O
• Isomeric SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=C(C=C4)N)I)O)O

Technology Process of I-AB-Meca

There total 4 articles about I-AB-Meca 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-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide (1053726-11-6) → (2S,3S,4R,5R)-5-[6-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide (152918-27-9)

Guidance literature:

With hydrogenchloride; at 70 ℃; for 1h; Yield given;

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) → (2S,3S,4R,5R)-5-[6-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide (152918-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1: CHCl₃ / 0.25 h / 10 °C

2: Et₃N / ethanol / 70 °C

3: 1N HCl / 1 h / 70 °C

With hydrogenchloride; triethylamine; In ethanol; chloroform;

DOI:10.1021/jm00031a014

Reference yield:

2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide (152918-47-3) → (2S,3S,4R,5R)-5-[6-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide (152918-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / ethanol / 70 °C

2: 1N HCl / 1 h / 70 °C

With hydrogenchloride; triethylamine; In ethanol;

DOI:10.1021/jm00031a014

upstream raw materials:

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

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

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

Refernces