The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-D-glucose as donors in glycosylation reactions.
1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-beta-D-glu copyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-alpha-D-glucopyra nosyl bromides have been used as donors in glycosylation reactions with model alcohols. beta-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity. An oxazolidinone was formed as the main product from the reaction of some of the glucopyranosyl bromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group.
Boullanger
P
P
Laboratoire de Chimie Organique II, C.N.R.S., Université de Lyon I, Villeurbanne, France.
Jouineau
M
M
Bouammali
B
B
Lafont
D
D
Descotes
G
G
D000438:Alcohols; D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis
D000438:Alcohols; D009844:Oligosaccharides; D005944:Glucosamine