3'-DEOXYGUANOSINE

Base Information

• Chemical Name: 3'-DEOXYGUANOSINE
• CAS No.: 3608-58-0
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.244
• Hs Code.: 29349990
• Mol file: 3608-58-0.mol

Synonyms:3'-Deoxyguanosine;Guanine, 9-(3-deoxy-b-D-erythro-pentofuranosyl)-;

Chemical Property of 3'-DEOXYGUANOSINE

Chemical Property:

• Melting Point: <300℃ (water )
• Boiling Point: 725.5 °C at 760 mmHg
• Flash Point: 392.6 °C
• PSA: 140.01000
• Density: 2.08 g/cm³
• LogP: -1.72740
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Water (Slightly, Heated, Sonicated)

Purity/Quality:

97% ^*data from raw suppliers

3’-Deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: 3'-Deoxyguanosine (3'-CDG) is a carbocyclic nucleoside analogue that exhibits significant antiviral activity against herpes simplex virus types 1 and 2 (HSV-1 and HSV-2), demonstrating potency comparable to or exceeding that of ara-A, though it is less effective than acyclovir. Additionally, it shows modest activity against influenza virus. 3'-DEOXYGUANOSINE's structure, derived from modifications to the ribofuranoside backbone, contributes to its antiviral properties, making it a candidate for further investigation in antiviral therapy.

Technology Process of 3'-DEOXYGUANOSINE

There total 1 articles about 3'-DEOXYGUANOSINE 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:

2-n-acetyl-9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)guanine → 2',3'-dideoxyguanosine (85326-06-3) + 3'-deoxyguanosine (3608-58-0)

Guidance literature:

With sodium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₃CN;

DOI:10.1080/07328319608002368

Reference yield: 92.0%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 3'-deoxyguanosine (3608-58-0) → N'-[9-((2R,3R,5S)-3-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dimethyl-formamidine (869355-04-4)

Guidance literature:

In methanol;

DOI:10.1080/07328319708006156

Reference yield:

3'-deoxyguanosine (3608-58-0) → N3-(p-anisyldiphenylmethyl)-3'-deoxyguanosine (444019-18-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 53 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: 0.56 g / pyridine / 20 °C

3: 0.65 g / tetrabutylammonium fluoride/SiO₂ / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; silica gel; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm0495172

Downstream raw materials:

N'-[9-((2R,3R,5S)-3-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dimethyl-formamidine

N³-(p-anisyldiphenylmethyl)-3'-deoxyguanosine

N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl) (phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide

Diisopropyl-phosphoramidous acid (2R,3R,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Refernces

Synthesis and Antiviral Evaluation of Carboxylic Analogues of 2-Amino-6-substituted-purine 3'-Deoxyribofuranosides

10.1021/jm00389a019

The research focused on the synthesis and antiviral evaluation of carbocyclic analogues of 2-amino-6-substituted-purine 3'-deoxyribofuranosides. The purpose of the study was to develop compounds with potential antiviral activity against herpes simplex virus (HSV-1 and HSV-2) and influenza virus. The researchers synthesized a series of carbocyclic analogues, including 3'-deoxyguanosine (3'-CDG), 2-amino-6-chloropurine 3'-deoxyribofuranoside, and 2,6-diamino-8-azapurine 3'-deoxyribofuranoside, among others. The conclusions drawn from the study indicated that 3'-CDG showed significant activity against HSV-1 and HSV-2, with its activity being equal to or greater than that of ara-A, a positive-control drug. However, it was less potent than ara-A and less active than acyclovir. The compound also demonstrated modest activity against influenza virus. The chemicals used in the process included various purine and pyrimidine derivatives, as well as reagents like triethyl orthoformate, hydrochloric acid, and ammonia-methanol for the synthesis of the target compounds. The study also involved the use of analytical techniques such as UV, IR, MS, and NMR for characterization and the assessment of antiviral activity through in vitro tests.