78138-02-0

Upstream product

• 133658-23-8 (2R,3S)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 65-71-4 2,4-dihydroxy-5-methylpyrimidine 
• 100-39-0 benzyl bromide 
• 63593-01-1 3'-O-benzyl-2'-deoxythymidine 
• 50-89-5 thymidine 
• 7791-71-1 5'-O-tritylthymidine 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 6160-49-2 1-O-acetyl-3,5-di-O-benzyl-2-deoxy-D-erythro-pentofuranose 
• 132487-16-2 methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 
• 6160-50-5 3,5-di-O-benzyl-2-deoxy-D-ribofuranose 
• 270918-00-8 (2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-chloro-tetrahydro-furan 

Downstream Products

• 137121-87-0 α/β-D-thymidine 

Relevant academic research and scientific papers

In search of Flavivirus inhibitors part 2: Tritylated, diphenylmethylated and other alkylated nucleoside analogues

Several flaviviruses, such as the yellow fever virus and the dengue virus cause severe and potentially lethal infection in man. Following up on our initial hit 3′,5′-bistritylated uridine 1, a series of alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against dengue fever virus and yellow fever virus. Hereto, alkyl and aryl groups were attached at various positions of the sugar ring combined with subtle variation of the heterocyclic base. Among the new series of derivatives, 3′,5′-di-O-trityl-5-fluoro-2′-deoxyuridine (39) was the most efficient in this series and inhibited both yellow fever virus and dengue virus replication with a 50% effective concentration (EC50) of ～1 μg/mL without considerable cytotoxicity. The other fluorinated derivatives proved more toxic. Almost all diphenylmethylated pyrimidine nucleosides with 3′,5′-di-O-benzhydryl-2′-deoxyuridine (50) as the example were endowed with strong cytotoxic effects down to 1 μg/mL.

Efficient electrochemical N-glycosylation of silylated pyrimidines with protected arylthioriboses in the presence of a catalytic amount of NBS or Br2

Electrolysis of silylated pyrimidines with protected arylthioribose, in the presence of a catalytic amount of NBS or Br2 as a mediator in an undivided cell, gave the corresponding N-glycosides (nucleosides) in good yield.

Stereoselective Synthesis of β-2-Deoxyribonucleosides from 1-O-Acetyl-3-O--2-deoxyribose

β-2-Deoxyribonucleosides are prepared stereoselectively from 1-O-acetyl-5-O-benzyl-3-O--2-deoxy-D-erythro-pentofuranose by the reaction with the silyl or zinc derivatives of nucleoside bases in the presence of trimethylsilyl trifl

STEREOCHEMICAL CONTROL AS A FUNCTION OF PROTECTING-GROUP PARTICIPATION IN 2-DEOXY-D-ERYTHRO-PENTOFURANOSYL NUCLEOSIDES

Possible features controlling the anomeric ratios in the synthesis of the antiviral antibiotic dihydro-5-azathymidine have been examined.Replacement of the 3- and 5-(4-methylbenzoyl) protecting groups in 2-deoxy-D-erythro-pentofuranosyl chloride by benzyl