125344-77-6Relevant academic research and scientific papers
Phospho Sugars; Novel Preparation and Their Glycosyl Compounds
Ikai, Koichi,Iida, Akihito,Yamashita, Mitsuji
, p. 595 - 597 (1989)
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.
Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2- phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars
Yamada, Manabu,Yamashita, Mitsuji,Suyama, Takuya,Yamashita, Junko,Asai, Kazuhide,Niimi, Taishi,Ozaki, Nobuhisa,Fujie, Michio,Maddali, Kasthuraiah,Nakamura, Satoki,Ohnishi, Kazunori
experimental part, p. 5943 - 5946 (2010/11/18)
4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (2c) by a bromo-radical substitution reaction occurred at C-4 position by N-bromosuccinimide and 2,2′-azobisisobutyronitrile. The novel phospha sugar analogue 3c exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec, which is known as a molecule targeting chemotherapeutical agent. The substitution of 2-phospholenes at C-3 and C-4 position with methyl groups as well as 4-bromo substituent suggests a good anti-proliferative effect.
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.
