Synthesis of novel amino acid glycoside conjugates

A new class of non-anomeric amino acid glycoconjugates can be prepared starting from either ω-amino- or ω-halodeoxyglucosides. Treatment of an ether-protected methyl 7-amino-6,7-dideoxy-α-d-glucoheptopyranoside with methyl aspartate isocyanate gave an urea-linked conjugate of methyl glucoheptopyranoside and aspartic acid. Nucleophilic displacement of the ether-protected methyl 6-chloro-6-deoxy-α-d-glucopyranoside with potassium succinimide followed by imide ring opening and amidation of the succinic acid monoamide with dimethyl iminodiacetate led to a conjugate of methyl 6-amino-6-deoxy-α-d-glucopyranoside and iminodiacetate bridged by succinate.