7-DEAZAGUANOSINE

Base Information

• Chemical Name: 7-DEAZAGUANOSINE
• CAS No.: 102731-45-3
• Molecular Formula: C₁₁H₁₄N₄O₅
• Molecular Weight: 282.256
• Mol file: 102731-45-3.mol

Synonyms:9-Deazaguanosine

Chemical Property of 7-DEAZAGUANOSINE

Chemical Property:

• Melting Point: 259-264°C
• PKA: 11.33±0.20(Predicted)
• PSA: 157.48000
• Density: 2.15±0.1 g/cm3(Predicted)
• LogP: -1.43140
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol, Water

Purity/Quality:

97% ^*data from raw suppliers

9-Deazaguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A guanosine analogue.

Technology Process of 7-DEAZAGUANOSINE

There total 3 articles about 7-DEAZAGUANOSINE 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: 75.0%

2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one (864155-80-6) → 9-deazaguanosine (102731-45-3)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature; pH 13;

DOI:10.1021/jm00172a011

Reference yield:

9-deazaguanine (65996-58-9) → 9-deazaguanosine (102731-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / SnCl₄ / nitromethane / 3 h / 60 °C

2: 75 percent / NaOMe / methanol / Ambient temperature; pH 13

With sodium methylate; tin(IV) chloride; In methanol; nitromethane;

DOI:10.1021/jm00172a011

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (14215-97-5) → 9-deazaguanosine (102731-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / SnCl₄ / nitromethane / 3 h / 60 °C

2: 75 percent / NaOMe / methanol / Ambient temperature; pH 13

With sodium methylate; tin(IV) chloride; In methanol; nitromethane;

DOI:10.1021/jm00172a011

upstream raw materials:

2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one

9-deazaguanine

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

Downstream raw materials:

2-isobutyrylamino-7-[5-tert-butyldiphenylsilyl-2,3-bis-O-(methylthio)thiocarbonyl-β-D-ribofuranosyl]-5H-pyrrolo[3,2-d]pyrimidin-4-one

2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-2,3-O-thiocarbonyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one

2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one

2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-2,3-didehydro-2,3-dideoxy-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one

Refernces

• 1、 Girgis, Nabih S.,Michael, Maged A.,Smee, Donald F.,Alaghamandan, Hassan A.,Robins, Roland K.,Cottam, Howard B.. "Direct C-Glycosylation of Guanine Analogues: The Synthesis and Antiviral Activity of Certain 7- and 9-Deazaguanine C-Nucleosides". . p. 2750 - 2755. Retrieved 2007/10/02.