Intersaccharidic bonds

H. Kunz and C. Unverzagt, Protecting group-dependent stability of intersaccharide bonds— synthesis of a fucosyl-chitobiose glycopeptide, Angew. Chem. lnt. Ed. Engl. 27 1697 (1988). 

Kunz, H. and Unverzagt, C. (1988) Protecting-group-dependant stability of intersaccharide bonds-Synthesis of a fucosyl-chitobiose glycopeptide. Angew. Chem. Int. Ed. 27, 1697-1699. 

Oxygen Nucleophile. Uchiro et al. have reported hydrolysis of a thioglycoside bond under very mild conditions using the combination of tetrabutylammonium periodate as oxidant, trityl tetrakis(pentafluorophenyl)borate as Lewis acid catalyst, and HMDO in anhydrous acetonitrile at 0 °C (eq 17). The reaction also proceeded well in the absence of HMDO, using aqueous tri-flic or perchloric acid as catalyst in place of the trityl derivative. The intersaccharidic bond of a disaccharide was found to be stable under these conditions, with no anomerization being observed. 

Figure 5. Intersaccharide hydrogen bonds (dotted lines) and the glycosidic angle 0 (05-01-04 -04 ) between site A and B. These hydrogen bonds and 0 (= -86 ) are similar to those found for cellulose.

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