6-Thioinosine 5'-phosphate

Base Information

• Chemical Name: 6-Thioinosine 5'-phosphate
• CAS No.: 53-83-8
• Molecular Formula: C10H13 N4 O7 P S
• Molecular Weight: 364.276
• NSC Number: 520722
• Mol file: 53-83-8.mol

Synonyms:6-Thioinosine 5'-phosphate;6-Mercaptopurine riboside-5-phosphate;SCHEMBL15810629;SCHEMBL20266286;NSC520722;FT-0675168;9H-Purine-6-thiol, 5'-(dihydrogen phosphate)

Chemical Property of 6-Thioinosine 5'-phosphate

Chemical Property:

• Melting Point: 149-155°C (dec.)
• Boiling Point: 833.4°Cat760mmHg
• Flash Point: 457.9°C
• PSA: 208.66000
• Density: 2.25g/cm³
• LogP: -1.15650
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly, Sonicated)
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 364.02425694
• Heavy Atom Count: 23
• Complexity: 559

Purity/Quality:

97% ^*data from raw suppliers

6-Thioinosine Phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=S)C2=C(N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O
• Uses: A metabolite of 6-Mercaptopurine.

Technology Process of 6-Thioinosine 5'-phosphate

There total 16 articles about 6-Thioinosine 5'-phosphate 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: 86.0%

2',3'-O-isopropylidene-5'-O-(di-tert-butylphosphoramidite)-6-thioinosine (1375103-71-1) → 6-thioinosine 5'-monophosphate (53-83-8,22974-34-1,58328-93-1)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 24h;

DOI:10.1021/jm201127y

Reference yield: 55.0%

Phosphoric acid (3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-thioxo-1,6-dihydro-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester bis-(2,2,2-tribromo-ethyl) ester (78681-85-3) → 6-thioinosine 5'-monophosphate (53-83-8,22974-34-1,58328-93-1)

Guidance literature:

With Nafion 125; lithium perchlorate; In N,N-dimethyl-formamide; acetonitrile; electrolysis;

DOI:10.1055/s-1981-29501

Reference yield:

6-chloropurine riboside 5'-monophosphate (5843-59-4,59126-39-5) → 6-thioinosine 5'-monophosphate (53-83-8,22974-34-1,58328-93-1)

Guidance literature:

With water; potassium hydrosulfide;

DOI:10.1021/ja01462a030

upstream raw materials:

6-chloropurine riboside 5'-monophosphate

5-phosphoribosyl-1-pyrophosphate

6-mercaptopurine

Phosphoric acid (3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-thioxo-1,6-dihydro-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester bis-(2,2,2-tribromo-ethyl) ester

Downstream raw materials:

methylthioinosine monophosphate

Refernces

• 1、 Moreau, Christelle,Kirchberger, Tanja,Zhang, Bo,Thomas, Mark P.,Weber, Karin,Guse, Andreas H.,Potter, Barry V. L.. "Aberrant cyclization affords a C-6 modified cyclic adenosine 5′-diphosphoribose analogue with biological activity in Jurkat T cells". . p. 1478 - 1489. Retrieved 2012/04/23.
• 2、 Engels, Joachim,Krahmer, Ute. "Bis Phosphorochloridate: A Suitable Phosphorylating Agent for Nucleosides". . p. 485 - 486. Retrieved 2007/10/02.