27552-66-5

Basic information

• Product Name: Guanosine, 5'-O-(triphenylmethyl)-
• CAS NO: 27552-66-5
• Molecular Formula: C29H27N5O5
• Molecular Weight: 525.564
• Mol File: 27552-66-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Guanosine, 5'-O-(triphenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Guanosine, 5'-O-(triphenylmethyl)-(27552-66-5)
• EPA Substance Registry System: Guanosine, 5'-O-(triphenylmethyl)-(27552-66-5)

Safety Data

• Hazardous Substances Data: 27552-66-5(Hazardous Substances Data)

Upstream product

• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 5333-62-0 benzyl trityl ether 
• 118-00-3 G 

Downstream Products

• 86404-83-3 N'-[9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dimethyl-formamidine 

Relevant articles and documents

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.