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Synthesis 1989; 1989(8): 595-597
DOI: 10.1055/s-1989-27328
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Phospho Sugars; Novel Preparation and Their Glycosyl Compounds

Koichi Ikai* , Akihito Iida, Mitsuji Yamashita
  • *Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, Hamamatsu 432, Japan
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Publikationsdatum:
17. September 2002 (online)

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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-phospholenc 1-oxide by bromination and nucleophilic substitution reactions. This is a novel and excellent route to prepare phospho sugar derivatives.