457653-20-2

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 18055-46-4 bis(trimethylsilyl)-N⁶-benzoyladenine 
• 209048-62-4 1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-4-thio-D-erythro-pento-1-enitol 
• 60855-35-8 6-benzoylamino-9-trimethylsilylpurine 
• 134938-97-9 benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 
• 457653-07-5 benzyl 2-deoxy-3,5-O-(di-tert-butylsilylene)-1,4-dithio-D-erythro-pentofuranoside 
• 209048-57-7 benzyl 3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 
• 209048-59-9 1,4-anhydro-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-D-erythro-pent-1-enitol 
• 4005-49-6 N-benzoyladenine 
• 134700-25-7 (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol 

Relevant academic research and scientific papers

Stereoselective synthesis of the β-anomer of 4′-thionucleosides based on electrophilic glycosidation to 4-thiofuranoid glycals

Three types of 4-thiofuranoid glycal with different 3,5-O-silyl protecting groups were prepared and their electrophilic glycosidation was investigated. The 3,5-bis-O-(tert-butyldimethylsilyl)-4-thiofuranoid glycal (5) was obtained through mesylation of 2-deoxy-4-thio-D-erythro-pentofuranose (4) and subsequent base-promoted elimination, while thermal elimination of sulfoxide derivatives was suitable for the preparation of 3,5-O-(tetraisopropyldisiloxane-1,3-diyl) (9) and 3,5-O-(di-tert-butylsilylene) (11) 4-thioglycals. The glycosidation reactions of these 4-thioglycals were carried out, in the presence of either PhSeCl or NIS, by using silylated derivatives of uracil, thymine, cytosine, and N6-benzoyladenine. Among the three 4-thioglycals, 11 was found to be an excellent glycosyl donor, forming the desired β-anomer exclusively irrespective of the nucleobase employed.