Journal of the American Chemical Society, Vol.120, No.7, 1392-1397, 1998
Synthesis of the hexasaccharide fragment of landomycin A: Application of glycosyl tetrazoles and phosphites in the synthesis of a deoxyoligosaccharide
The synthesis of the hexasaccharide fragment of the antitumor antibiotic landomycin A (1) (aka. NSC 639187) is described. The stereocontrolled introduction of key glycoside linkages relies on the combined application of glycosyl tetrazoles and phosphites to establish alpha and beta glycosidic linkages, respectively. Spectral comparison of landomycin A octaacetate (2) and hexasaccharide pentaacetate (3) serves to corroborate the assigned structure of 1 within the oligosaccharide domain.