77755-66-9Relevant articles and documents
RECTIVITE COMPAREE DE DIVERS ACCEPTEURS DE LA D-GLUCOSAMINE LORS DE LA SYNTHESE DE PRECURSEURS DU CHITOBIOSE
Lafont, Dominique,Boullanger, Paul,Fenet, Bernard
, p. 565 - 584 (2007/10/02)
Six D-glucosamine derivatives, diversely substituted at the nitrogen atom, were tested as acceptors in glycosylation reactions with 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranose (1) as the donor and trimethylsilyl trifluoromethanesulfonate as the promoter.The observed yields were high with 2-phthalimido- and 2-azido-D-glucosamine acceptors and more generally good with acceptors of the 1,6-anhydro-D-glucosamine series.The disaccharides benzyl 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (20), benzyl 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-2-allyloxycarbonylamino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (21), 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (22), 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-2-allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (23), 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (24) and 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (25) have thus been synthesized.