Journal of Organic Chemistry p. 5192 - 5199 (1993)
Update date:2022-07-29
Topics: Characterization Purification Stereochemical Control Protecting Group Manipulation Starting Material - Carbohydrate Derivative Ring Closure to Form Oxazolidine Introduction of the Thio Group (Sulfur Atom) Ring Expansion to Bicyclic Oxazine-2-thione
Fernandez, Jose M. Garcia
Mellet, Carmen Ortiz
Fuentes, Jose
Chiral, sugar-derived oxazolidine-2-thiones having a pseudo-C-nucleoside structure, as well as bicyclic 2-thioxotetrahydro-1,3-oxazines, have been prepared by intramolecular cyclization of 6-deoxy-6-isothiocyanatoaldoses or -aldopyranosides, respectively.The reaction proceeds with total regioselectivity and no need for protection of the secondary hydroxyl groups.A one-pot procedure for the synthesis of the five-membered heterocycles from the corresponding amino sugars is aslo reported.The six-membered analogs have a cis- or trans-decalin-type core depending on the configuration of the sugar precursor.
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