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Synthesis of a glucosylated α-S-galactosylceramide (1), a potential immunostimulant, was achieved starting from D-galactose. Both O- and S-glycosidic linkages were constructed in highly stereoselective way, and the synthetic strategy could be extended to the synthesis of other α-S-GalCer analogues.
A ring-closing metathesis approach was employed for the synthesis of a β-C-glycoside analog of the immunostimulant KRN7000. The protected C-glycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the...
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