237410-14-9Relevant academic research and scientific papers
Synthesis of 2-fluoro-substituted and 2,6-modified purine 2′,3′-dideoxy-2′,3′-difluoro-D-arabinofuranosyl nucleosides from D-xylose
Sivets, Grigorii G.,Amblard, Franck,Schinazi, Raymond F.
, p. 2037 - 2046 (2019/02/27)
A series of novel purine-modified 2′,3′-dideoxy-2′,3′-difluro-D-arabinonucleosides, including fluorinated analogs of fludarabine and nelarabine, have been prepared via anion glycosylation reactions of salts of 2-fluoropurine derivatives with the glycosyl bromide. A short and efficient synthetic route to the carbohydrate precursor 5-O-benzoyl-2,3-difluoro-α-D-arabinofuranosyl bromide was developed in five steps from D-xylose. Improved synthesis of methyl 5-O-benzoyl-2,3-difluoro-α-D-arabinofuranoside based upon the study of diethylaminosulfur trifluoride (DAST)-reactions with 5-O-protected methyl D-xylosides was explored using mild reaction conditions on the key step. New peculiarities for selective fluorinations of 5-O-benzoylated α- and β-D-pentofuranosides with DAST leading to the formation of mono and difluoro-furanoside derivatives are reported.
Synthesis and antiviral activity of purine 2',3'-dideoxy-2',3'-difluoro-D- arabinofuranosyl nucleosides
Sivets, Grigorii G.,Kalinichenko, Elena N.,Mikhailopulo, Igor A.,Detorio, Mervi A.,McBrayer, Tami R.,Whitaker, Tony,Schinazi, Raymond F.
experimental part, p. 519 - 536 (2010/10/02)
9-(2',3'-Dideoxy-2',3'-difluoro-D-arabinofuranosyl)adenine (20), 2-chloro-9-(2',3'-dideoxy-2,3-difluoro-D-arabinofuranosyl)adenine (22), as well as their respective -anomers 21 and 23, were synthesized by the nucleobase anion glycosylation of intermediate
Synthesis of 9-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)adenine
Sivets, Grigorii G.,Kalinichenko, Elena N.,Mikhailopulo, Igor A.
, p. 1387 - 1389 (2008/09/17)
Convergent synthesis of 9-(2,3-dideoxy-2,3-difluoro-β-D- arabinofuranosyl)adenine is described starting from methyl 5-O-benzyl-2-deoxy-2- fluoro-α-D-arabinofuranoside. Copyright Taylor & Francis Group, LLC.
A novel route for the synthesis of fluorodeoxy sugars and nucleosides
Mikhailopulo, Igor A.,Sivets, Grigorii G.,Khripach, Natalia B.
, p. 689 - 690 (2007/10/03)
Ring-fluorination of α- and β-D-pentofuranosides containing free secondary hydroxyl groups by (diethylamino)sulfur trifluoride (DAST) was studied.
A novel route for the synthesis of deoxy fluoro sugars and nucleosides
Mikhailopulo, Igor A.,Sivets, Grigorii G.
, p. 2052 - 2065 (2007/10/03)
The reaction of (diethylamino)sulfur trifluoride (DAST) with methyl 5-O- benzoyl-β-D-xylofuranoside (1) followed by column chromatography afforded the riboside 2 (62%) and the ribo-epoxide 3 (18%) (Scheme 1). Under similar reaction conditions, the α-D-ano
