22596-01-6

Basic information

• Product Name: 5'-O-(Triphenylmethyl)cytidine
• Synonyms: 5'-O-(Triphenylmethyl)cytidine
• CAS NO: 22596-01-6
• Molecular Formula: C₂₈H₂₇N₃O₅
• Molecular Weight: 485.53
• Mol File: 22596-01-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5'-O-(Triphenylmethyl)cytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(Triphenylmethyl)cytidine(22596-01-6)
• EPA Substance Registry System: 5'-O-(Triphenylmethyl)cytidine(22596-01-6)

Safety Data

• Hazardous Substances Data: 22596-01-6(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 65-46-3 CYTIDINE 
• 41028-66-4 1,5-anhydroribitol 
• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 71-30-7 Cytosine 

Downstream Products

• 86404-82-2 N'-[1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethyl-formamidine 
• 65-46-3 CYTIDINE 
• 192314-87-7 (2S,3S,4S,5R)-5-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-2-trityloxymethyl-tetrahydro-furan-3-carbonitrile 
• 192314-88-8 (2S,5R)-5-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile 
• 192314-86-6 4-Amino-1-((1S,2R,4R,5S)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-2-yl)-1H-pyrimidin-2-one 

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.