Synthesis of 2-fluoro-substituted and 2,6-modified purine 2',3'-dideoxy-2',3'-difluoro-d-arabinofuranosyl nucleosides from d-xylose.
Tetrahedron
; 75(13): 2037-2046, 2019 Mar 29.
Article
em En
| MEDLINE
| ID: mdl-34316083
ABSTRACT
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 ß-D-pentofuranosides with DAST leading to the formation of mono and difluoro-furanoside derivatives are reported.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article