6-Methylmercaptopurine riboside

Base Information

• Chemical Name: 6-Methylmercaptopurine riboside
• CAS No.: 342-69-8
• Molecular Formula: C11H14 N4 O4 S
• Molecular Weight: 298.323
• Hs Code.: 29349990
• European Community (EC) Number: 206-442-2
• UNII: Y5G39SHR0V
• DSSTox Substance ID: DTXSID5030454
• Nikkaji Number: J53.894I
• Wikidata: Q27093868
• NCI Thesaurus Code: C2352
• Metabolomics Workbench ID: 56538
• ChEMBL ID: CHEMBL388931
• Mol file: 342-69-8.mol

Synonyms:6 Methylmercaptopurine Riboside;6 Methylthiopurine Riboside;6-Methylmercaptopurine Riboside;6-Methylthiopurine Riboside;Methylthioinosine;Riboside, 6-Methylmercaptopurine;Riboside, 6-Methylthiopurine

Chemical Property of 6-Methylmercaptopurine riboside

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 4.6E-17mmHg at 25°C
• Melting Point: 166°C
• Refractive Index: 1.6270 (estimate)
• Boiling Point: 636.3°Cat760mmHg
• Flash Point: 338.6°C
• PSA: 138.82000
• Density: 1.85g/cm³
• LogP: -0.84030
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 298.07357611
• Heavy Atom Count: 20
• Complexity: 352

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Methylmercaptopurine Riboside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)O)O
• Isomeric SMILES: CSC1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• Uses: 6-Methylmercaptopurine Riboside (cas# 342-69-8) is a compound useful in organic synthesis. 6-Methylmercaptopurine riboside (6MMPr) is used in studies on thiopurine metabolism by enzymes such as inosine-5′-monophosphate dehydrogenase and thiopurine methyltransferase. 6MMPr may also be used to study mechanisms of bovine viral diarrhea virus (BVDV) inhibition.

Technology Process of 6-Methylmercaptopurine riboside

There total 17 articles about 6-Methylmercaptopurine 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: 94.0%

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(1,2,4-triazol-4-yl)purine (158782-62-8) + sodium thiomethoxide (5188-07-8) → 6-methylmercaptopurine riboside (342-69-8)

Guidance literature:

In N,N-dimethyl-formamide; for 0.25h; Ambient temperature;

Reference yield: 42.0%

6-Chloropurine riboside (2004-06-0) + carbonic acid dimethyl ester (616-38-6) → 6-methylmercaptopurine riboside (342-69-8)

Guidance literature:

With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate; In dimethyl sulfoxide; at 120 ℃; Inert atmosphere;

Reference yield:

triacetyladenosine (7387-57-7,953089-09-3) → 6-methylmercaptopurine riboside (342-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / 20 h / 100 °C

2: 94 percent / dimethylformamide / 0.25 h / Ambient temperature

With pyridine; In N,N-dimethyl-formamide;

upstream raw materials:

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(methylthio)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(1,2,4-triazol-4-yl)purine

sodium thiomethoxide

6-mercaptopurine riboside

Downstream raw materials:

kinetin riboside

(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furan-3-ol

2'-O-3'-O,N⁽⁴⁾-Triacetylarabinofuranosylcytidylyl 5'-(2',3'-di-O-isopropylidene-6-methylthiopurine riboside), 5'-(2-chlorophenyl)phosphate

Phosphoric acid 2-chloro-phenyl ester (3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester; compound with triethyl-amine

Refernces

• 1、 -. "Methyl aryl thioether compound, and synthetic method and applications thereof". Paragraph 0152; 0153; 0154. . Retrieved 2017/07/21.
• 2、 -. "Anti-HCV nucleoside derivatives". . . Retrieved 2008/06/13.