62160-23-0

Basic information

• Product Name: 7-DEAZAGUANOSINE
• Synonyms: 2-Amino-3,5-dihydro-7-β-D-ribofuranosyl-4H-pyrrolo[3,2-d]pyrimidine-4-one;2-Amino-7-(β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one;2-Amino-1,7-dihydro-7-β-D-ribofuranosyl-4H-pyrrolo[2,3-d]pyrimidin-4-one;2-Amino-7-(β-D-ribofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidine-4-one;2-Amino-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-4(3H)-one;7-β-D-Ribofuranosyl-2-amino-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one;4H-Pyrrolo2,3-DpyriMidin-4-one,2-aMino-1,7-dihydro-7-B-D-ribofuranosyl-;7-DEAZAGUANOSINE
• CAS NO: 62160-23-0
• Molecular Formula: C₁₁H₁₄N₄O₅
• Molecular Weight: 282.25
• Product Categories: Nucleotides;Bases & Related Reagents
• Mol File: 62160-23-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: >250°C dec
• Boiling Point: 668.3°Cat760mmHg
• Flash Point: 358°C
• Appearance: /
• Density: 2.06g/cm³
• Vapor Pressure: 9.05E-19mmHg at 25°C
• Refractive Index: 1.874
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol
• PKA: 11.29±0.20(Predicted)
• CAS DataBase Reference: 7-DEAZAGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-DEAZAGUANOSINE(62160-23-0)
• EPA Substance Registry System: 7-DEAZAGUANOSINE(62160-23-0)

Safety Data

• Hazardous Substances Data: 62160-23-0(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A guanosine analogue

InChI:InChI=1/C11H14N4O5/c12-11-13-8-4(9(19)14-11)1-2-15(8)10-7(18)6(17)5(3-16)20-10/h1-2,5-7,10,16-18H,3H2,(H3,12,13,14,19)/t5-,6-,7-,10-/m1/s1

Upstream product

• 115479-41-9 2-amino-4-methoxy-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 115479-40-8 4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine 
• 115479-42-0 2-Amino-4-methoxy-7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidine 
• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 
• 41028-66-4 1,5-anhydroribitol 
• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 7355-55-7 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 102690-95-9 5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl chloride 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 76567-71-0 2-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 80153-19-1 3,7-Dihydro-3-(isopropoxymethyl)-2-methylthio-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 80153-20-4 2-(Acetylamino)-3,7-dihydro-3-(isopropoxymethyl)-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 120401-36-7 2-amino-4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 151072-85-4 2-<<(dimethylamino)methylidene>amino>-7-<5-O-(4-methoxytrityl)-β-D-ribofuranosyl>-3H-pyrrolo<2,3-d>-pyrimidin-4(7H)-one 
• 141692-17-3 7-<5-O-(4-methoxytrityl)-β-D-ribofuranosyl>-2-<(2-methylpropanoyl)amino>-3H-pyrrolo<2,3-d>-pyrimidin-4(7H)-one 
• 151072-88-7 2-<<(dimethylamino)methylidene>amino>-7-<5-O-(4-methoxytrityl)-2-O--β-D-ribofuranosyl>-3H-pyrrolo<2,3-d>pyrimidin-4(7H)-one 

Relevant articles and documents

C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents

African trypanosomiasis, a deadly infectious disease caused by the protozoan Trypanosoma brucei spp., is spread to new hosts by bites of infected tsetse flies. Currently approved therapies all have their specific drawbacks, prompting a search for novel th

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.

2,4-Disubstituted pyrrolo[2,3-d]pyrimidine α-D- and β-D-ribofuranosides related to 7-deazaguanosine

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