Facile syntheses of pseudo-α-d-arabinofuranose, and two pseudo-d-arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-β-d-arabinofuranosyluracil, from d-arabinose

Autor: Shoko Yamaguchi, Masayuki Yoshikawa, Yasunao Inoue, Isao Kitagawa, Y. Yokokawa, Nobutoshi Murakami
Rok vydání: 1994
Předmět:
Zdroj: Tetrahedron. 50:9961-9974
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89611-3
Popis: An optically active pseudo-sugar, pseudo-α- d -arabinofuranose, was efficiently synthesized from d -arabinose by using a stereoselective nitromethane addition reaction to form a branched nitropyranose (6) as a key step. Furthermore, two biologically active pseudo-β- d -arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-β- d -arabinofuranosyluracil, were also synthesized from the nitrocyclopentene derivative (12), which was prepared from a synthetic intermediate of pseudo-arabinofuranose, via Michael-type reaction introducing nucleic acid base moieties.
Databáze: OpenAIRE