4-Amino-4-cyano-4,6-dideoxy sugar derivatives from methyl 6-deoxy-2,3-O-isopropylidene-α-l-lyxo-hexopyranosid-4-ulose via Strecker-type reaction

Application of the Strecker reaction to methyl 6-deoxy-2,3-O-isopropylidene-α-l-lyxo-hexopyranosid-4-ulose resulted in the formation of methyl 4-amino-4-cyano-4,6-dideoxy-2,3-O-isopropylidene-α-l-talopyranoside, methyl 4-amino-4-cyano-4,6-dideoxy-2,3-O-isopropylidene-β-d-allopyranoside and methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-α-l-talopyranoside. Their proportionality and yields depend on the reaction conditions used. Additionally, 4-amino-4-cyano-4,6-dideoxy-2,3-O-isopropylidene-α-l-talopyranoside can be prepared favourably from preformed methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-α-l-talopyranoside. The crystal structure of methyl 4-acetamido-4-cyano-4,6-dideoxy-2,3-O-isopropylidene-α-l-talopyranoside is also presented.