N-p-methoxybenzylidene derivatives of 2-amino-2-deoxy-D-glucose as glycosyl donors: a reinvestigation.
6-O-Acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-D- glucopyranosyl chloride, 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-alpha-D-glu copyranosyl bromide, 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-alpha- and -beta-D- glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2-p-nitrobenzylideneamino-alpha-D-gluco pyranosyl bromide have been synthesised, and their behaviour as glycosylation agents with various soluble promoters has been investigated. The results obtained question the accepted non-participating character of the N-p-methoxybenzylideneamino group.
Marra
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Laboratoire de Chimie, UA 1110, Paris, France.
Sinaÿ
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D001597:Benzylidene Compounds; D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D005944:Glucosamine / Q000031:analogs & derivatives*; D006031:Glycosylation; D008745:Methylation; D008969:Molecular Sequence Data
D001597:Benzylidene Compounds; D005944:Glucosamine