A new reaction for the direct conversion of 4-azido-4-deoxy-D-galactoside into a 4-deoxy-D-erythro-hexos-3-ulose.
[reaction: see text] A new one-step reaction has been developed for converting 4-azido-4-deoxy-d-galactoside into 4-deoxy-d-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the phosphite intermediate and a tetrazole-catalyzed elimination reaction of the resultant phosphorimidate. Tetrazole appears to be playing a unique role by acting as a bifunctional catalyst to facilitate the elimination reaction.
Xue
Jie
J
Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, Ohio 44106-7078, USA.
Wu
Jian
J
Guo
Zhongwu
Z
D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003837:Deoxy Sugars / Q000138:chemical synthesis / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D005697:Galactosides / Q000138:chemical synthesis / Q000737:chemistry*; D007094:Imides / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry
C493206:4-azido-4-deoxy-D-galactoside; C493207:4-deoxy-D-erythro-hexos-3-ulose; D001386:Azides; D003837:Deoxy Sugars; D004852:Epoxy Compounds; D005697:Galactosides; D007094:Imides; D013777:Tetrazoles; C045574:1H-tetrazole