6-Thioguanosine

Base Information

• Chemical Name: 6-Thioguanosine
• CAS No.: 85-31-4
• Molecular Formula: C10H13 N5 O4 S
• Molecular Weight: 299.31
• Hs Code.: 29349990
• European Community (EC) Number: 201-597-2
• UNII: C558LI0K8P
• DSSTox Substance ID: DTXSID201018977
• Nikkaji Number: J4.914J
• Wikidata: Q27166529
• ChEMBL ID: CHEMBL283078
• Mol file: 85-31-4.mol

Synonyms:2-amino-9-beta-D-ribofuranosyl-9H-purine-6-thiol;6-mercaptoguanosine;6-thioguanosine;6-thioguanosine, (beta-D)-isomer

Chemical Property of 6-Thioguanosine

Chemical Property:

• Appearance/Colour: Yellow-Green Powder
• Vapor Pressure: 3.44E-24mmHg at 25°C
• Melting Point: 230-231°C
• Refractive Index: 1.6460 (estimate)
• Boiling Point: 756.9 °C at 760 mmHg
• PKA: 13.21±0.70(Predicted)
• Flash Point: 411.6 °C
• PSA: 174.53000
• Density: 2.18 g/cm³
• LogP: -0.73620
• Storage Temp.: -20°C Freezer
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 299.06882509
• Heavy Atom Count: 20
• Complexity: 449

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

6-Thioguanosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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)NC(=NC2=S)N
• Isomeric SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=NC2=S)N
• Uses: antineoplastic

Technology Process of 6-Thioguanosine

There total 6 articles about 6-Thioguanosine 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:

O2',O3',O5'-tribenzoyl-6-thio-guanosine (88010-92-8) → 6-thioguanosine (85-31-4)

Guidance literature:

With sodium ethanolate;

DOI:10.1021/ja01540a041

Reference yield:

2',3',5'-tri-O-benzoylguanosine (66048-53-1) → 6-thioguanosine (85-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous pyridine; P₂S₅

2: ethanolic sodium ethylate

With pyridine; tetraphosphorus decasulfide; sodium ethanolate;

DOI:10.1021/ja01540a041

Reference yield:

G (118-00-3) → 6-thioguanosine (85-31-4)

Guidance literature:

With pyridine; sodium hydrogensulfide; trifluoroacetic anhydride; Multistep reaction; 1) 40 min, ice-bath, 2) DMF, 24 h;

DOI:10.1016/0040-4039(91)80589-X

upstream raw materials:

O^2'_,O3'_,O5'-tribenzoyl-6-thio-guanosine

G

2',3',5'-tri-O-benzoylguanosine

6-thioguanine

Downstream raw materials:

2-amino-9-β-D-ribofuranosylpurine-6-sulfonamide

3-deazasulfinosine

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

Refernces

• 1、 -. "Anti-HCV nucleoside derivatives". . . Retrieved 2008/06/13.