Synthesis of a tetrasaccharide repeating unit of O-antigenic polysaccharide of Salmonella enteritidis by use of unique and odorless dodecyl thioglycosyl donors

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The first total synthesis of a unique tetrasaccharide repeating unit of lipopolysaccharide from Salmonella enteritidis has been accomplished by assembly of dodecyl thioglycosides. The crucial key steps were preparation of a rare branched dideoxy sugar, D-tyvelose (3,6-dideoxy-D-arabino-D-hexose) and sequential regioselective glycosylation at 2,3-positions of a central D-mannose residue 5 with D-tyvelose 6 and D-galactose donors 7.
2008-09-01