A new, stereocontrolled approach to iminosugar C-glycosides from L-sorbose.
The efficient synthesis of the iminoalditols derivatives 1 and 2 (nojirimycin alpha-C-glycosides) has been achieved in 10 steps from commercially available 2,3;4,6-di-O-isopropylidene-alpha-L-sorbofuranose in an overall yield of 23-27%.
Masson
G
G
Institut de Chimie Organique et Analytique, Faculté des Sciences, BP 6759, 45067 Orléans Cedex 2, France.
Compain
P
P
Martin
O R
OR
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006027:Glycosides / Q000138:chemical synthesis; D016695:Glycosyltransferases / Q000037:antagonists & inhibitors; D018716:Molecular Mimicry; D013013:Sorbose / Q000737:chemistry*; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D006027:Glycosides; D017485:1-Deoxynojirimycin; D016695:Glycosyltransferases; D006026:Glycoside Hydrolases; D005944:Glucosamine; D013013:Sorbose; C013626:nojirimycin