Synthesis of carbohydrates with an anomeric thiol moiety for elaboration into metabolically stable thioglycosides

Citation
Mj. Kiefel et al., Synthesis of carbohydrates with an anomeric thiol moiety for elaboration into metabolically stable thioglycosides, J CARB CHEM, 18(8), 1999, pp. 937-959
Citations number
49
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
18
Issue
8
Year of publication
1999
Pages
937 - 959
Database
ISI
SICI code
0732-8303(1999)18:8<937:SOCWAA>2.0.ZU;2-J
Abstract
The synthesis of thioglycosides for use as metabolically stable biological probes is an area of continued interest. This paper describes the synthesis of functionalised carbohydrates which contain an anomeric thio group. Duri ng the course of this work we have examined the most viable route into comp ounds such as the specifically functionalised carbohydrates 36 and 37, and have also investigated the usefulness of disulfides as protecting groups fo r anomeric thiols.