241490-75-5Relevant academic research and scientific papers
Glycosylation of Branched Amino and Nitro Sugars. 2. Synthesis of the Cororubicin Trisaccharide
Noecker, Lincoln,Duarte, Franco,Bolton, Scott A.,McMahon, Wayne G.,Diaz, Maria T.,Giuliano, Robert M.
, p. 6275 - 6282 (2007/10/03)
The synthesis of the nitro-sugar-containing trisaccharide found in the antibiotic cororubicin is described. This trisaccharide contains the nitro sugar L-decilonitrose which is attached to two digitoxose residues (a dideoxy sugar) by β-1,4 and α-1,4 linkages. The target trisaccharide synthesized was methyl 2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1-→4)-2,3,6-trideoxy-3-C-methyl- 3-nitro-β-L-ribo-hexopyranosyl-(1-→4)-2,6-dideoxy-α-L-lyxo- hexopyranoside. The principle features of the synthesis are the use of an O-benzylhydroxylamino sugar as the precursor to the nitro sugar decilonitrose and as both the acceptor and donor in glycosyations, a β-selective glycosylation by means of a thioglycoside donor, and novel functional group transformations carried out on the assembled trisaccharide. These include oxidative cleavage of the O-benzylhydroxylamino group to nitro, carried out with dimethyldioxirane in one step. This transformation proved critical in completing the synthesis, which is the first reported of one of the decilonitrose-containing trisaccharides found in antibiotics.
