6-Chloroguanosine

Base Information

• Chemical Name: 6-Chloroguanosine
• CAS No.: 2004-07-1
• Molecular Formula: C10H12ClN5O4
• Molecular Weight: 301.689
• Hs Code.: 29349990
• European Community (EC) Number: 217-905-3
• Nikkaji Number: J199.813G
• Wikidata: Q27456329
• ChEMBL ID: CHEMBL244169
• Mol file: 2004-07-1.mol

Synonyms:2004-07-1;6-Chloroguanosine;2-Amino-6-chloropurine-9-riboside;6-Chloroguanineriboside;6-Chloroguanine riboside;(2R,3R,4S,5R)-2-(2-Amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;2-Amino-6-chloropurine riboside;2-Amino-6-chloro-9-(beta-D-ribofuranosyl)purine;(2R,3R,4S,5R)-2-(2-amino-6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;6-Chloro-9-beta-D-ribofuranosyl-9H-purin-2-amine;6-Chloro-9-(Beta-D-Ribofuranosyl)-9h-Purin-2-Amine;9H-Purin-2-amine, 6-chloro-9-beta-D-ribofuranosyl-;MFCD00005735;(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;(-)-2-Amino-6-chloropurine riboside;SCHEMBL637420;CHEMBL244169;2-Amino-6-chloropurine ribosid;EINECS 217-905-3;NSC 44586;2-Amino-6-chloropurine Ribonucleoside;AKOS015854915;AKOS015896934;GS-3225;(3S,2R,4R,5R)-5-(2-amino-6-chloropurin-9-yl)-2-(hydroxymethyl)oxolane-3,4-diol;2-Amino-6-chloropurine-9-?-D-riboside;2-Amino-6-chloropurine riboside, >=95%;2-Amino-6-chloro-9-(b-D-ribofuranosyl)purine;EN300-1704270;6-chloro-2-amino-9-(beta-D-ribofuranosyl)purine;2-Amino-6-chloro-9-(b-D-ribofuranosyl)-9H-purine;Q27456329;(4S,2R,3R,5R)-2-[2-amino-6-chloro-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol;6CR

Chemical Property of 6-Chloroguanosine

Chemical Property:

• Appearance/Colour: colourless crystalline solid
• Vapor Pressure: 2.3E-22mmHg at 25°C
• Melting Point: 165-167 °C (dec.)(lit.)
• Refractive Index: -38 ° (C=0.1, H2O)
• Boiling Point: 729.9 °C at 760 mmHg
• PKA: 13.05±0.70(Predicted)
• Flash Point: 395.2 °C
• PSA: 139.54000
• Density: 2.19 g/cm³
• LogP: -0.74540
• Storage Temp.: −20°C
• Solubility.: DMSO, Methanol
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 301.0577816
• Heavy Atom Count: 20
• Complexity: 367

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-6-chloropurine-9-b-D-riboside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC2=C(N1C3C(C(C(O3)CO)O)O)N=C(N=C2Cl)N
• Isomeric SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(N=C2Cl)N
• Uses: 6-Substituted purines; a novel class of inhibitors of endogenous protein degradation

Technology Process of 6-Chloroguanosine

There total 20 articles about 6-Chloroguanosine 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: 93.0%

7-methylguanosine hydroiodide (81100-62-1) + 2-Amino-6-chloropurin (10310-21-1) → 2-Amino-6-chloropurine riboside (2004-07-1) + 7-methylguanine (578-76-7)

Guidance literature:

With recombinant purine nucleoside phosphorylase from Aeromonas hydrophila; at 20 ℃; pH=7.5; regioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/adsc.201100505

Reference yield: 93.0%

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6) → 2-Amino-6-chloropurine riboside (2004-07-1)

Guidance literature:

With ammonia; at 20 ℃;

DOI:10.1002/adsc.201100505

Reference yield: 90.3%

2,6-dichloropurine riboside (13276-52-3) → 2-Amino-6-chloropurine riboside (2004-07-1)

Guidance literature:

With ammonia; at 25 ℃; for 12h; Temperature;

upstream raw materials:

2-amino-6-chloro-9-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>purine

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

methanol

2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine

Downstream raw materials:

2-amino-N⁶-(2-methyl-benzyl)-adenosine

2-amino-N⁶-(2-phenyl-propyl)-adenosine

2-amino-N⁶-[2''-(p-hydroxyphenyl)ethyl]adenosine

2-amino-N⁶-(2-methoxy-benzyl)-adenosine

Refernces

• 1、 Kikugawa,K. et al.. "-". . p. 387 - 390. Retrieved 1972.
• 2、 Bhattarai, Sanjay,Pippel, Jan,Scaletti, Emma,Idris, Riham,Freundlieb, Marianne,Rolshoven, Georg,Renn, Christian,Lee, Sang-Yong,Abdelrahman, Aliaa,Zimmermann, Herbert,El-Tayeb, Ali,Müller, Christa E.,Str?ter, Norbert. "2-Substituted α,β-Methylene-ADP Derivatives: Potent Competitive Ecto-5′-nucleotidase (CD73) Inhibitors with Variable Binding Modes". supporting information. p. 2941 - 2957. Retrieved 2020/04/10.
• 3、 Collier, Alice,Wagner, Gerd K.. "Base-modified GDP-mannose derivatives and their substrate activity towards a yeast mannosyltransferase". . p. 91 - 96. Retrieved 2017/10/30.