133832-78-7Relevant articles and documents
Synthesis of Chiral Building Blocks from D-Glucosamine Hydrochloride
Giannis, Athanassios,Henk, Thomas
, p. 789 - 793 (2007/10/02)
Wittig-reaction of 2-acetamido-2-deoxy-D-glucose (1) with the semistabilized ylide Ph3P=CHPh yielded the epimeric chain-elongated derivatives 2 and 3 in different amounts depending on the reaction conditions.Reaction of 2-(tert-butoxycarbonylamino)-2-deoxy-D-glucose (5) with Ph3P=CHPh yielded the compound 8, or after intramolecular cyclisation, the derivatives 6 or 7.Compound 3 was transformed in three steps into the amino alcohol 10.The 3-amino-1,2-diol derivative 17 and also the N,O-protected α-hydroxy-β-amino acid derivative 16 were obtained from 7.The N-protected homophenylalanine derivatives 12 and 14 were available in two steps from 2 or 8. - Key Words: Amino sugars / Amino alcohols / Amino acids / Wittig reaction