Synthesis of N-Linked Glycosyl Asparagine Derivatives with Unprotected Sugar Components

Abstract

A general methodology for the efficient formation of N-glycosidic linkage to asparagine (Asn), which, does not require the protection of sugar component hydroxyl groups is described. Aspartic acid fluoride was used in combination with N-allyloxycarbonyl (Alloc) glycosyl amines. Pd(0)-PhSiH₃ mediated in situ Alloc removal-coupling was performed in aqueous solution dioxane to give Asn-linked carbohydrates in high yield.

Key words

asparagine - carbohydrate - aspartic acid fluoride - glycosylamine - allyl carbamate

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