22596-01-6

Upstream product

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

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 academic research and scientific papers

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.

Synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine; A unique antiviral nucleoside

The synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine 1 was accomplished using two different approaches. First, uridine and cytidine were used to prepare the key intermediate epoxides 15 and 31 which were opened with cyanide, deoxygenated by elimination to vinyl nitriles 17 and 36, and reduced by 1,4 hydride addition to the saturated nitriles 18 and 37. Secondly, a novel Rh-catalyzed hydroformylation reaction of 2',3'-didehydro-2',3'-dideoxycytidine 46 was used to prepare 1 in four steps. The attempted use of 2'-deoxyuridine and 2'-deoxycytidine to prepare 1 is also discussed.