O-Glycoside formation

A. F. Bochkov and G. E. Zaikov, Chemistry of the O-Glycosidic Bond Formation and Cleavage, Pergamon Press, Oxford, 1979. 

Similarly, ketose sugars participate in polysaccharide formation by reaction of their ano-meric carbon with a hydroxyl of another monosaccharide to create a ketal linkage. The acetal and ketal bonds within polysaccharides are termed o-glycosidic linkages. 

III. 3-6>-Glycopeptides of l-Serine or l-Threonine 1. Formation of the 3-O-Glycosidic Linkage... 

Newer Observations on the Synthesis of O-Glycosides 1. Formation of Furanosides )... 

In the synthesis of analogues of calicheamicin 71 and esperamicin Ajb, Moutel and Prandi employed the glycosyla-tion of a nitrone with a trichloroacetimidate as a key step - /3-N-O glycosidic bond formation. Preparation of the nitrone begins with the alkylation of the known alcohol 69 <1992CC1494> with 1,4-dibromobutane in the presence of sodium hydride. Subsequent aminoalkylation, amine protection with 9-fluorenylmethoxycarbonyl (Fmoc), and reduction with NaBHsCN were followed by nitrone 70 formation with 4-methoxybenzaldehyde (Scheme 8) <2001J(P1)305>. 

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