Purin-6-yl 1-thio-beta-glucopyranosiduronic acid

Base Information

• Chemical Name: Purin-6-yl 1-thio-beta-glucopyranosiduronic acid
• CAS No.: 63425-02-5
• Molecular Formula: C11H12N4O6S
• Molecular Weight: 328.3012
• DSSTox Substance ID: DTXSID10212839
• Wikidata: Q83088050
• Mol file: 63425-02-5.mol

Synonyms:ammonium 7H-purin-6-yl 1-thio-beta-glucopyranosiduronate;purin-6-yl 1-thio-beta-glucopyranosiduronic acid

Chemical Property of Purin-6-yl 1-thio-beta-glucopyranosiduronic acid

Chemical Property:

• Vapor Pressure: 5.85E-29mmHg at 25°C
• Boiling Point: 826.8°Cat760mmHg
• PKA: 2.85±0.70(Predicted)
• Flash Point: 453.9°C
• PSA: 186.98000
• Density: 1.9g/cm³
• LogP: -1.66280
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 328.04775529
• Heavy Atom Count: 22
• Complexity: 431

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1)C(=NC=N2)SC3C(C(C(C(O3)C(=O)O)O)O)O
• Isomeric SMILES: C1=NC2=C(N1)C(=NC=N2)S[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O

Technology Process of Purin-6-yl 1-thio-beta-glucopyranosiduronic acid

There total 4 articles about Purin-6-yl 1-thio-beta-glucopyranosiduronic acid 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:

methyl 7H-purin-6-yl 1-thio-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (82971-03-7) → (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(7H-purin-6-ylsulfanyl)-tetrahydro-pyran-2-carboxylic acid (63425-02-5)

Guidance literature:

With potassium hydroxide; In methanol; for 3h;

DOI:10.1021/jm00354a024

Reference yield:

6-Mercaptopurine (157930-09-1,157930-10-4,157930-11-5,157930-13-7,157930-14-8) → (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(7H-purin-6-ylsulfanyl)-tetrahydro-pyran-2-carboxylic acid (63425-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / K₂CO₃ / dimethylformamide; benzene / 8 h / Ambient temperature

2: aq. KOH / methanol / 3 h

With potassium hydroxide; potassium carbonate; In methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00354a024

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(7H-purin-6-ylsulfanyl)-tetrahydro-pyran-2-carboxylic acid (63425-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / K₂CO₃ / dimethylformamide; benzene / 8 h / Ambient temperature

2: aq. KOH / methanol / 3 h

With potassium hydroxide; potassium carbonate; In methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00354a024

upstream raw materials:

methyl 7H-purin-6-yl 1-thio-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate

6-Mercaptopurine

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester