Synthesis of N-acylated 7-amino-2,6,7-trideoxy-D-erythroheptopyranosides from methyl alpha-D-mannoside.
Hexopyranoside methyl alpha-D-mannoside (8) was homologated to yield 7-(acylamino)-2,6,7-trideoxy-heptopyranosides 19-26. A crucial reaction step is the radical cleavage of benzylidene derivative 10 to obtain bromide 11. Since nucleophilic substitution of 11 with KCN provided the bicyclic nitrile 13 instead of nitrile 14, ketone 11 was protected as the dimethyl acetal 15. Nucleophilic substitution of 15 with KCN, subsequent hydrogenation with H2/Raney Ni and acylation with various carboxylic acid derivatives yielded 7-(acylamino)heptopyranosides 19-22.
Wiedemeyer
Kathrin
K
Institut für Pharmazeutische und Medizinische Chemie der Westfälischen Wilhelms-Universität Münster, Hittorfstrasse 58-62, D-48149 Münster, Germany.
Wünsch
Bernhard
B
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D008766:Methylmannosides / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
D000606:Amino Sugars; D003837:Deoxy Sugars; D008766:Methylmannosides; C008466:methylmannoside