FACILE SYNTHESES OF PSEUDO-ALPHA-D-ARABINOFURANOSE, AND 2 PSEUDO-D-ARABINOFURANOSYLNUCLEOSIDES, (-CYCLARADINE AND (+)-1-PSEUDO-BETA-D-ARABINOFURANOSYLURACIL, FROM D-ARABINOSE())
M. Yoshikawa et al., FACILE SYNTHESES OF PSEUDO-ALPHA-D-ARABINOFURANOSE, AND 2 PSEUDO-D-ARABINOFURANOSYLNUCLEOSIDES, (-CYCLARADINE AND (+)-1-PSEUDO-BETA-D-ARABINOFURANOSYLURACIL, FROM D-ARABINOSE()), Tetrahedron, 50(33), 1994, pp. 9961-9974
An optically active pseudo-sugar, pseudo-alpha-D-arabinofuranose, was
efficiently synthesized from D-arabinose by using a stereoselective ni
tromethane addition reaction to form a branched nitropyranose (6) as a
key step. Furthermore, two biologically active pseudo-beta-D-arabinof
uranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-beta-D-arabinofu
ranosyluracil, were also synthesized from the nitrocyclopentene deriva
tive (12), which was prepared from a synthetic intermediate of pseudo-
arabinofuranose, via Michael-type reaction introducing nucleic acid ba
se moieties.