Arabinosyl-6-mercaptopurine

Base Information

• Chemical Name: Arabinosyl-6-mercaptopurine
• CAS No.: 574-25-4
• Molecular Formula: C10H12 N4 O4 S
• Molecular Weight: 284.296
• Hs Code.: 29349990
• NSC Number: 406021,99193,92429,92428,84321,4911
• Mol file: 574-25-4.mol

Synonyms:arabinosyl 6 mercaptopurine;arabinosyl-6-mercaptopurine

Chemical Property of Arabinosyl-6-mercaptopurine

Chemical Property:

• Vapor Pressure: 1.99E-17mmHg at 25°C
• Melting Point: 220-223 °C(lit.)
• Refractive Index: 1.6270 (estimate)
• Boiling Point: 714.7°Cat760mmHg
• PKA: 8.40±0.20(Predicted)
• Flash Point: 386°C
• PSA: 148.51000
• Density: 2.02g/cm³
• LogP: -0.89960
• Storage Temp.: -20°C
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 284.05792605
• Heavy Atom Count: 19
• Complexity: 409

Purity/Quality:

99% ^*data from raw suppliers

6-Mercaptopurine-9-b-D-ribofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=S)C2=C(N1)N(C=N2)C3C(C(C(O3)CO)O)O
• Uses: A substrate for adenosine deaminase A substrate for adenosine deaminase.

Technology Process of Arabinosyl-6-mercaptopurine

There total 26 articles about Arabinosyl-6-mercaptopurine 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: 95.0%

6-thio-9-(2',3',5'-tri-O-acetyl-β-D-ribosyl)purine (3021-21-4) → 6-mercaptopurine riboside (574-25-4)

Guidance literature:

With methanol; water; triethylamine; at 71 ℃; Microwave irradiation;

DOI:10.1590/S0103-50532010000500013

Reference yield: 85.4%

2',3',5'-tri-O-benzoyl-6-thioinosine (6741-90-8) → 6-thioinosine (574-25-4)

Guidance literature:

With sodium hydroxide; In pyridine; methanol; at 20 ℃; for 0.0833333h;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2094::AID-HLCA2094>3.0.CO;2-H

Reference yield: 85.0%

6-Chloropurine riboside (2004-06-0) → 6-thioinosine (574-25-4)

Guidance literature:

With thiourea; In ethanol; at 50 ℃; for 8h;

DOI:10.1021/acs.orglett.0c03241

upstream raw materials:

6-Chloropurine riboside

thiourea

2',3',5'-tri-O-benzoyl-6-thioinosine

nitrobenzylthioinosine

Downstream raw materials:

6-methylmercaptopurine riboside

6-benzylthio-purine riboside

Nebularin

2',3'-O-isopropylidene-6-thioinosine

Refernces

• 1、 Johnson,Thomas. "-". . p. 3863. Retrieved 1956.
• 2、 -. "Heterocyclic compound containing SCF3 or SeCF3, and preparation method thereof". Paragraph 0097-0100. . Retrieved 2020/07/12.
• 3、 Del Arco, Jon,Mills, Alberto,Gago, Federico,Fernández-Lucas, Jesús. "Structure-Guided Tuning of a Selectivity Switch towards Ribonucleosides in Trypanosoma brucei Purine Nucleoside 2′-Deoxyribosyltransferase". . p. 2996 - 3000. Retrieved 2019/11/11.