496048-32-9

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 496048-25-0 (2S,3S)-[difluoro(2-hydroxymethyl-5-oxotetrahydrofuran-3-yl)methyl]phosphonic acid diethyl ester 
• 496048-24-9 tert-butyl 2,3-dideoxy-3-[(diethoxyphosphoryl)difluoromethyl]-4,5-O-(1-methylethylidene)-D-glyceropentonate 
• 496048-30-7 (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-oxotetrahydrofuran-3-yl]difluoromethyl}phosphonothioic acid O,O-diethyl ester 
• 496048-26-1 (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-oxotetrahydrofuran-3-yl]difluoromethyl}phosphonic acid diethyl ester 

Downstream Products

• 675147-64-5 benzoic acid (2S,3S,5R)-3-[(diethoxythiophosphoryl)difluoromethyl]-5-ethoxytetrahydrofuran-2-ylmethyl ester 
• 675147-66-7 benzoic acid (2S,3S,5S)-3-[(diethoxythiophosphoryl)difluoromethyl]-5-ethoxytetrahydrofuran-2-ylmethyl ester 
• 496048-33-0 (4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate 

Relevant academic research and scientific papers

N-Glycosylation of 2,3-dideoxyfuranose derivatives having a (diethoxyphosphorothioyl)difluoromethyl group at the 3α-position

Lewis acid-mediated N-glycosylation of 2,3-dideoxyribofunanosides having a (diethoxyphosphorothioyl)difluoromethyl group at the 3α-position with silylated nucleobases was examined. The phosphorothioyldifluoromethyl was found to be an effective functional group for the diastereoselective synthesis of β-N1-pyrimidine-nucleotide analogues 26 and 28-30. However, the method was not useful for the diastereoselective synthesis of adenine nucleotide analogues. The nucleotide analogue 26 was transformed to the difluoromethylenephosphonate analogue 31 of thymidine-3′-phosphate by oxidation with m-CPBA, followed by aqueous work-up.

N-glycosylation of 2,3-dideoxyfuranose derivatives having difluoromethylene-phosphonate and -phosphonothioate functionality at the 3α-position

TiCl4-Mediated N-glycosylation of 2,3-dideoxyribofunanosides having a difluoromethylene-phosphonate or -phosphonothioate functional group at the 3α-position with silylated pyrimidines was examined. The phosphonate functional was a good directin