Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

Beilstein Journal of Organic Chemistry

Inmaculada Robina¹  Elena Moreno-Clavijo¹  Jens Frigell²  Elias Pershagen²  Ian Cumpstey²  Tashfeen Akhtar²  Terry D. Butters³  Dominic S. Alonzi³ 

[1] Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof. García González, 1, 41012 Seville, Spain;Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden;Glycobiology Institute, Department of Biochemistry, Oxford University, South Parks Road, Oxford, OX1 3QU, England;

关键词: amination;    glycomimetics;    glycosidases;    Mitsunobu;    pseudodisaccharides;   

DOI  :  10.3762/bjoc.7.128

来源: DOAJ

【 摘 要 】

Diglycose derivatives, consisting of two monosaccharides linked at non-anomeric positions by a bridging nitrogen atom, have been synthesised. Conversion of one of the precursor 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 diglycosides. The amine-linked diglycosides were found to show weak glycosidase inhibitory activity.

【 授权许可】

Unknown