Azaguanosine

Base Information

• Chemical Name: Azaguanosine
• CAS No.: 2133-80-4
• Molecular Formula: C₉H₁₂N₆O₅
• Molecular Weight: 284.231
• Mol file: 2133-80-4.mol

Synonyms:3H-v-Triazolo[4,5-d]pyrimidin-7-ol,5-amino-3-b-D-ribofuranosyl- (6CI); 7H-v-Triazolo[4,5-d]pyrimidin-7-one,5-amino-3,6-dihydro-3-b-D-ribofuranosyl- (7CI,8CI); 8-Azaguanosine; NSC 130283; NSC 46788

Chemical Property of Azaguanosine

Chemical Property:

• Vapor Pressure: 3.13E-15mmHg at 25°C
• Melting Point: 250-252 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 567.3°C at 760 mmHg
• PKA: 8.32±0.20(Predicted)
• Flash Point: 296.9°C
• PSA: 172.40000
• Density: 2.49g/cm³
• LogP: -2.71050

Purity/Quality:

97% ^*data from raw suppliers

8-AZAGUANOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 8-Azaguanosine is an azapurine nucleoside.An extensive study has been made of the fluorescence emission properties of the neutral and ionic forms in aqueous medium of the 8-Azaguanosine. The 8-?azaguanosine is a substrate of purine nucleoside phosphorylase (PNP)?.

Technology Process of Azaguanosine

There total 10 articles about Azaguanosine 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:

8-azaguanine (134-58-7) + α-D-ribofuranosyl-1-phosphate (18646-11-2) → 8-azaguanosine (2133-80-4)

Guidance literature:

With ammonium; E_. coli purine-nucleoside phosphorylase; In aq. buffer; at 25 ℃; for 3h; pH=7.3; Enzymatic reaction;

DOI:10.3390/molecules181012587

Reference yield:

[(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate (38874-35-0) → 8-azaguanosine (2133-80-4)

Guidance literature:

With ammonia; In methanol; at 50 ℃; for 16h;

DOI:10.1021/jo061885l

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 8-azaguanosine (2133-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 0.08 h / 130 °C / microwave irradiation

2: NH₃ / methanol / 16 h / 50 °C

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; ammonia; In methanol; acetonitrile; 1: Vorbrueggen glycosylation;

DOI:10.1021/jo061885l

upstream raw materials:

2-methylsulfanyl-8-aza-inosine

[(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate

ribofuranose-1-phosphate

8-azaguanine

Downstream raw materials:

8-Aza-xanthosin

Refernces

• 1、 Stachelska-Wierzchowska, Alicja,Wierzchowski, Jacek,Bzowska, Agnieszka,Wielgus-Kutrowska, Beata. "Site-Selective ribosylation of fluorescent nucleobase analogs using purine-Nucleoside phosphorylase as a catalyst: effects of point mutations". . . Retrieved 2016/02/05.
• 2、 Bookser, Brett C.,Raffaele, Nicholas B.. "High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries". . p. 173 - 179. Retrieved 2007/10/03.