Stereoselective synthesis of 2-amino-2-deoxysugars: N-alkyl-D-allosamines.
Stereoselective synthesis of N-alkyl-D-allosamines, designed for the preparation of N-alkyl derivatives of allosamidin (a chitinase inhibitor), is achieved by a 'carbonyl group transfer' reaction followed by stereoselective reduction and this method represents the first example of N-alkyl-D-allosamines synthesized from a 2-oxosugar.
Liu
Hong-Min
HM
Department of Chemistry, Zhengzhou University, Zhengzhou 450052, P. R. China. liuhm@public.zz.ha.cn
Zhang
Fuyi
F
Wang
Shaomin
S
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002688:Chitinases / Q000037:antagonists & inhibitors; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014312:Trisaccharides / Q000737:chemistry
D000606:Amino Sugars; D003837:Deoxy Sugars; D005960:Glucosides; D014312:Trisaccharides; C433386:allosamine; C054851:allosamidin; D002688:Chitinases; D005944:Glucosamine; D000117:Acetylglucosamine