Amino sugars and their mimetics via 1,2-oxazines.
This tutorial review covers recent research from our laboratory towards the synthesis of amino sugars and related carbohydrate mimetics employing 1,2-oxazines as crucial intermediates. The synthesis of new dideoxyamino carbohydrate derivatives, C2-branched 4-amino sugars and their mimetics, as well as sialic acid analogues, has been developed during the last few years. The results demonstrate that alkoxyallenes are ideal and versatile components for the chain elongation of carbohydrate derivatives. Our routes starting from 3,6-dihydro-2H-1,2-oxazines are presented in conjunction with two related examples from the recent literature. Finally, we discuss possible future applications of the described compounds as anti-inflammatory agents.
Pfrengle
Fabian
F
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.
Reissig
Hans-Ulrich
HU
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D000606:Amino Sugars / Q000138:chemical synthesis / Q000737:chemistry*; D003837:Deoxy Sugars / Q000138:chemical synthesis / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D010078:Oxazines / Q000737:chemistry*; D012794:Sialic Acids / Q000138:chemical synthesis / Q000737:chemistry
D000596:Amino Acids; D000606:Amino Sugars; D003837:Deoxy Sugars; D004187:Disaccharides; D010078:Oxazines; D012794:Sialic Acids