N-linked neodisaccharides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibitory activity
(English)Manuscript (preprint) (Other academic)
Neodisaccharides consisting of two monosaccharides linked by a bridging nitrogen atom have been synthesised. Converting one of the monosaccharide coupling components into an unsaturated derivative enhances its electrophilicity at the allylic position, facilitating coupling reactions. Mitsunobu coupling between nosylamides and 2,3-unsaturated 4-alcohols gave the 4-amino pseudodisaccharides with inversion of configuration as single regio- and diastereoisomers. A palladium catalysed coupling between an amine and a 2,3-unsaturated 4-trichloroacetimidate gave a 2-amino pseudodisaccharide as the major product along with other minor products. Derivatisation of the C=C double bond in pseudodisaccharides allowed the formation of Man(N4–6)Glc and Man(N4–6)Man neodisaccharides. The inhibitory activity of some N-linked neodisaccharides against the enzyme α-Glucosidase II is reported.
neodisaccharide, mitsunobu, N-linked, pseudodisaccharide, allylic alcohol, nosylamide, triflamide, Ferrier reaction, alkene functionalisation, alkene oxidation, asymmetric dihydroxylation, dihydroxylation, alfa-glucosidase, glucosidase II
Organic Chemistry Organic Chemistry
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-44221OAI: oai:DiVA.org:su-44221DiVA: diva2:360458