Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives. Org Lett 2020 Jun 05;22(11):4156-4159
Date
05/21/2020Pubmed ID
32432478Pubmed Central ID
PMC7493207DOI
10.1021/acs.orglett.0c01236Scopus ID
2-s2.0-85085703259 (requires institutional sign-in at Scopus site) 24 CitationsAbstract
Thioglycosides are more resistant to enzymatic hydrolysis than their O-linked counterparts, thereby becoming attractive targets for carbohydrate-based therapeutic development. We report the first development of methods for the site-selective incorporation of S-linkages into automated solution-phase oligosaccharide protocols. The protocols were shown to be compatible with the formation of S- or O-glycosides for the synthesis of mannopyranoside trimmers that incorporate both S- and O-linkages to allow the selective incorporation of an S-glycoside in various stages in an automated program.
Author List
Kern MK, Pohl NLBAuthor
Mark K. Kern Research Scientist II in the Medicine department at Medical College of WisconsinMESH terms used to index this publication - Major topics in bold
AutomationCarbohydrate Conformation
Glycosides
Mannose
Solutions
