Journal of Carbohydrate Chemistry p. 499 - 519 (1997)
Update date:2022-08-03
Topics:
Yamashita, Mitsuji
Yabui, Akihiro
Suzuki, Kazumitsu
Kato, Yukihiro
Uchimura, Miyuki
Iida, Akihito
Mizuno, Hiroyuki
Ikai, Koichi
Oshikawa, Tatsuo
Parkanayi, Laszlo
Clardy, Jon
Some phosphanyl sugar derivatives, which are analogs of sugars having a phosphorus atom in place of the ring oxygen, were synthesized from 2-and 3-phospholenes as starting materials. Catalytic cis-dihydroxylation of 2-phospholene or 3-phospholene 1-oxide derivatives with osmium(VIII) oxide in the presence of a cooxidant afforded 3-deoxy-or 1-deoxy-tetrofuranose-type phosphanyl sugar derivatives, respectively. cis-Dihydroxylation of 4-acyloxy-2-phospholene 1-oxide derivatives gave tetrofuranose type phosphanyl sugar derivatives. Some of these derivatives of phosphanyl sugars were subjected to structural analyses using 1H NMR and X-ray crystallography.
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