2-Aminopurine riboside

Base Information

• Chemical Name: 2-Aminopurine riboside
• CAS No.: 4546-54-7
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• Hs Code.: 2933599090
• Nikkaji Number: J647.930H
• ChEMBL ID: CHEMBL1651367
• Mol file: 4546-54-7.mol

Synonyms:2-Aminopurine riboside;4546-54-7;2-Amino Riboside;(2R,3R,4S,5R)-2-(2-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;CHEMBL1651367;2-amino-9-beta-d-ribofuranosylpurine;2-Amino-9-(b-D-ribofuranosyl)purine;(2R,3R,4S,5R)-2-(2-azanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;2-NH2-Riboside;SCHEMBL1494485;BDBM50335312;MFCD00037992;AS-47253;F12889;(2R,3R,4S,5R)-2-(2-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;OJI

Chemical Property of 2-Aminopurine riboside

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 2.88E-21mmHg at 25°C
• Melting Point: 105-115 °C
• Refractive Index: 1.907
• Boiling Point: 711.8oC at 760 mmHg
• Flash Point: 384.3oC
• PSA: 139.54000
• Density: 2.08 g/cm3
• LogP: -1.39880
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

99%, ^*data from raw suppliers

2-Aminopurine Riboside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C2C(=NC(=N1)N)N(C=N2)C3C(C(C(O3)CO)O)O
• Isomeric SMILES: C1=C2C(=NC(=N1)N)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• Uses: 2-Aminopurine Riboside is a probe of structural dynamics and charge transfer in DNA. Potential activator or inhibitor of B. anthracis spore germination.

Technology Process of 2-Aminopurine riboside

There total 16 articles about 2-Aminopurine riboside 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: 100.0%

2-Amino-6-chloropurine riboside (2004-07-1) → 2?amino?9?(β?D?ribofuranosyl)purine (4546-54-7)

Guidance literature:

With palladium hydroxide, 20 wt% on carbon; ammonium formate; In 1,4-dioxane; methanol; for 1h; Reflux;

DOI:10.1007/s00706-019-02502-7

Reference yield: 100.0%

6-mercaptoguanosine (85-31-4) → 2?amino?9?(β?D?ribofuranosyl)purine (4546-54-7)

Guidance literature:

nickel; In water; for 2h; Heating;

DOI:10.1021/jo00308a003

Reference yield: 96.0%

2-amino-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine (107037-21-8) → 2?amino?9?(β?D?ribofuranosyl)purine (4546-54-7)

Guidance literature:

With ammonia; In ethanol; at 25 ℃; for 23h;

DOI:10.1021/jo00383a034

upstream raw materials:

2-benzoylamidopurine

2-amino-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine

6-mercaptoguanosine

9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-ylamine

Downstream raw materials:

N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine

N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine

2-Iodo-9-<2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>purine

Refernces

• 1、 Bookser, Brett C.,Raffaele, Nicholas B.. "High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries". . p. 173 - 179. Retrieved 2007/10/03.
• 2、 Stimac,Muhic,Kobe. "A novel palladium-catalyzed deoxygenation of guanine O6-arenesulfonates. A practicable synthesis of 2-aminopurine nucleosides and related analogs". . p. 625 - 636. Retrieved 2007/10/02.