151075-97-7

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 70798-12-8 1,2-O-isopropylidene-3-O-benzyl-α-D-ribofuranoside 
• 190970-10-6 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose 
• 100-39-0 benzyl bromide 

Downstream Products

• 151076-11-8 3-O-Benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-1,2-O-isopropylidene-β-D-ribo-hexofuranose 
• 171360-31-9 diallyl (2-((3aR,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1,1-difluoroethyl)phosphonate 
• 131566-84-2 1,2-O-isopropylidene-3-O-benzyl-5-deoxy-α-D-ribofuranoside 

Relevant academic research and scientific papers

Synthesis of 5'-deoxy-5'-difluoromethyl phosphonate nucleotide analogs

A synthetic route to nucleoside 5'-deoxy-5'-difluoromethyl phosphonates from ribofuranosyl 5-deoxy-5-difluoromethyl phosphonate precursors is described. Methyl 5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-2,3-O- isopropylidene-β-D-ribo-hexofuranoside (7) was converted, under mild conditions, to the suitable glycosylating agent 1-O-acetyl-2,3-di-O-benzoyl-5,6-dideoxy-6-(diethoxyphosphinyl) -6,6-dif luoro-β-D-ribo-hexofuranoside (10). 1,2-Di-O-acetyl-3-O-benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)- 6,6-difl uoro-β-D-ribo-hexofuranoside (16) was also prepared as a versatile building block for nucleotide synthesis. Condensation of 10 with silylated nucleobases, followed by complete deprotection, afforded 5',6'-dideoxy-6'-(dihydroxyphosphinyl)-6',6'-difluoro nucleoside analogs 22a-c. In the case of the glycosylation of adenine, a considerable quantity of N-7 regioisomer 19 was formed. 5',6'-Dideoxy-6'-(dihydroxyphosphinyl)-6',6'-difluoro adenosine analog 22c was converted into the triphosphate analog 23 using 1,1'-carbonyldiimidazole activation followed by condensation with pyrophosphate. The adenosine 3',5'-cyclic monophosphate analog 24 was obtained through the DCC promoted intramolecular cyclization of 22c. Dinucleoside phosphate analog 27 was prepared by DCC-catalyzed coupling of 1-[2,3-di-O-benzoyl-5,6-dideoxy-6-(dihydroxyphosphinyl)-6,6- di fluoro-β-D-ribo-hexofuranosyl]uracil (21a) with 2',5'-bis(O-tert-butyldimethylsilyl)-N4-acetyl-cytidine (25), followed by deprotection.

Study of 1-deoxy-D-xylulose-5-phosphate reductoisomerase: Synthesis and evaluation of fluorinated substrate analogues

(Chemical Equation Presented) 1-Deoxy-D-xylulose-5-phosphate (DXP) reductoisomerase is a NADPH-dependent enzyme catalyzing the conversion of DXP to methyl-D-erythritol 4-phosphate (MEP). In this study, each of the hydroxyl groups in DXP and one of its C-1

Displacement of sugar triflates with C-nucleophiles: D-glucopyranose and D-ribofuranose chain extension and functionalization

Treatment of methyl 4-O-benzyl-2,3-di-O-methoxymethyl-6-O- trifluoromethanesulfonyl-α-D-glucopyranoside 1 or 3-O-benzyl-1,2-O- isopropylidene-5-O-trifluoromethenesulfonyl-α-D-ribofuranoside 2 with a variety of functionalized C-nucleophiles in THF-HMPA lea

Synthesis of (α,α-Difluoroalkyl)phosphonates by Displacement of Primary Triflates

Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl(lithiodifluoromethyl)phosphonate to provide the corresponding (α,α-difluoroalkyl)phosphonates in minutes at -78 deg C.