Disaccharides aminodeoxy, synthesis

Methods for the Synthesis of Aminodeoxy and Deoxy Disaccharides Related to -Trehalose... 

Amino sugars are components of antibiotic substances109 and bacterial polysaccharides,1,0 and are therefore of interest. The nucleoside antibiotics amicetin, bamicetin, and plicacetin contain, as the sugar residue, a monoaminopentadeoxy disaccharide that is closely related to maltose. In view of the reported antibiotic and antitumor properties of these pyrimidine nucleosides,111,112 the synthesis of aminodeoxy derivatives of maltose would be of interest. 

Simple one-pot synthesis of different 1-0-glycosylboranophosphate diesters (65), the stable analogues of 1-0-glycosylphosphates based on the anomeric H-phosphonate of a-L-rhamnopyranose as common precursor, has been reported. Various phosphodisaccharides, structural analogues of phosphate (66) including deoxy, fluoro and aminodeoxy disaccharide phosphates e.g. (67) have been synthesized. These phosphodisaccharides were tested as acceptor sub-strate/putative inhibitors for the Leishmania-a-D-mannosylphosphate transferase. 

Hirama has reviewed the application of intramolecular conjugate additions of y- and fi-carbamoyloxy-a,j8-unsaturated esters fc.f , Vol.21, p.89) in the synthesis of a variety of aminodeoxy-sugars." Further anomalously coupled nucleosides, e.a.. isonucleosides (46), have been obtained by Michael-type addition of purines to unsaturated aldehydes (Scheme 13). complex amino-disaccharides have been synthesized by employing the cycloadducts... 

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