DISAL glycosyl donors for the synthesis of a linear hexasaccharide under mild conditions.
[reaction: see text] The new class of glycosyl donors with a methyl 3,5-dinitrosalicylate (DISAL) anomeric leaving group has proved efficient for glycosylation under strictly neutral, mildly basic, or mildly acidic conditions. Here, we report the synthesis of novel DISAL disaccharide glycosyl donors prepared by easy nucleophilic aromatic substitution. These DISAL donors proved efficient in the synthesis of a starch-related hexasaccharide under very mild conditions. Glycosylations proceeded with alpha-selectivity and were compatible with Trt protecting groups.
Petersen
Lars
L
Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800 Kgs. Lyngby, Denmark.
Laursen
Jane B
JB
Larsen
Kim
K
Motawia
M Saddik
MS
Jensen
Knud J
KJ
D002240:Carbohydrate Sequence; D003511:Cyclohexanols / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D012459:Salicylates / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003511:Cyclohexanols; D006027:Glycosides; D009844:Oligosaccharides; D012459:Salicylates