125344-85-6Relevant academic research and scientific papers
Novel synthesis and structure of phosphanyl sugar derivatives
Yamashita, Mitsuji,Yabui, Akihiro,Suzuki, Kazumitsu,Kato, Yukihiro,Uchimura, Miyuki,Iida, Akihito,Mizuno, Hiroyuki,Ikai, Koichi,Oshikawa, Tatsuo,Parkanayi, Laszlo,Clardy, Jon
, p. 499 - 519 (2007/10/03)
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.
Phospho Sugars; Novel Preparation and Their Glycosyl Compounds
Ikai, Koichi,Iida, Akihito,Yamashita, Mitsuji
, p. 595 - 597 (2007/10/02)
Treatment of 1-phenyl-2-, and -3-phospholene 1-oxides with N-bromosuccinimide affords 4-bromo-1-phenyl-2-phospholene 1-oxide.Substitution of the bromide with acetate, followed by stereoselective oxidation with osmium tetroxide and peracetylation with acetic anhydride/pyridine affords phospho sugar derivatives of tetrafuranose.Furthermore, N-, O-, and S-glycosyl compounds of phospho sugars can be prepared from 3-methyl-1-phenyl-2-phospholene 1-oxide by bromination and nucleophilic substitution reactions.This is a novel and excellent route to prepare phospho sugar derivatives.
