Some amino sugars structurally related to 6-deoxymannojirimycin precursors prepared from methyl 6-deoxy-2,3-O-isopropylidene-α-d-lyxo-hexofuranosid-5-ulose and methyl 2,3-O-isopropylidene-α-d-lyxo-pentodialdo-1,4-furanoside Original Research Article

Methyl (5S)-5-C-amino-5-cyano-5-deoxy-2,3-O-isopropylidene-α-d-lyxofuranoside has been synthesised from methyl 2,3-O-isopropylidene-α-d-lyxo-pentodialdo-1,4-furanoside, applying the Strecker synthesis. Analogously, methyl (5S) and (5R)-5-C-amino-5-cyano-5,6-dideoxy-2,3-O-isopropylidene-α-d-lyxo-hexofuranosides were prepared from methyl 6-deoxy-2,3-O-isopropylidene-α-d-lyxo-hexofuranosid-5-ulose. The 5-S configuration was unambigously determined by single-crystal X-ray diffraction analysis of corresponding N-acetyl derivatives. Conformations of five-membered rings are discussed. The conversion of N-acetylated amino nitriles to N-acetylamino acid ethyl ester and amide, respectivelly, is also described.