Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation

• Various hydroxysuccinimidyl and hydroxyphthalimidyl glycosides were synthesized.
• Salient features of gold-catalyzed glycosidation were applied.
• Alkynyl 1,2-orthoesters as glycosyl donors were exploited.
• The reaction was noticed to be high yielding, diastereoselective, and catalytic method.
• The protocol was found to be compatible for the synthesis of aminoxy derivatives of higher oligosaccharides also.

The O-glycosidation of hydroxysuccinimides and hydroxyphthalimides with a variety of aldose derived propargyl 1,2-orthoesters under the gold(III)-catalyzed glycosidation conditions is reported. A wide range of hydroxysuccinimidyl and hydroxyphthalimidyl glycosides were synthesized from corresponding glycosyl orthoesters including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well.

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