Benzylidene Acetal Fragmentation Route to 6-Deoxy Sugars: Direct Reductive Cleavage in the Presence of Ether Protecting Groups, Permitting the Efficient, Highly Stereocontrolled Synthesis of β-d-Rhamnosides from d-Mannosyl Glycosyl Donors. Total Synthesis of α-d-Gal-(1→3)-α-d-Rha-(1→3)- β-d-Rha-(1→4)-β-d-Glu-OMe, the Repeating Unit of the Antigenic Lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652
An approach to the stereocontrolled synthesis of beta-d-rhamnopyranosides is described in which 2,3-O-benzyl or related 4,6-O-[alpha-(2-(2-iodophenyl)ethylthiocarbonyl)benzylidene]-mannosyl thioglycosides are first used to introduce the beta-d-mannopyranoside linkage in high yield and stereoselectiv...
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Veröffentlicht in: | Journal of the American Chemical Society 2004-07, Vol.126 (26), p.8232-8236 |
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Sprache: | eng |
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