A Novel Method for the Synthesis of ddA and F-ddA Via Regioselective 2′-O-Deacetylation of 9-(2,5-DI-O-Acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine

Autor: Toshihide Yukawa, Kunisuke Izawa, Yasuhiro Tanaka, Hiroshi Shiragami, Yumiko Uchida, Hisao Iwagami
Rok vydání: 1992
Předmět:
Zdroj: Nucleosides and Nucleotides. 11:391-400
ISSN: 0732-8311
DOI: 10.1080/07328319208021713
Popis: Regioselective 2′-O-deacetylation of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine (1) is achieved by treatment of 1 with β-cyclodextrin (β-CyD) / aq. NaHCO3 or N2H4·H2O / EtOH. The 9-(5-O-Acetyl-3-bromo-3-deoxy-β-D-xylo-furanosyl)adenine (2) obtained is a common intermediate for the synthesis of 2′,3′-dideoxy-adenosine (ddA) (7) and 9-(2-fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-adenine (F-ddA) (9).
Databáze: OpenAIRE