Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl-carbohydrate derivatives

18Citations
Citations of this article
3Readers
Mendeley users who have this article in their library.
Get full text

Abstract

Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions (tBuOOH, Ti(OiPr)4, Et2iPrN). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-D-erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further reaction with PhSeH in the presence of BF3·Et2O. Erythro and threo furanoid glycals were also prepared by treating 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols under similar conditions. The 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols were obtained from 4-pentene-1,2,3-triols by a 5-endo selenium electrophilic induced cyclization. © 2001 Published by Elsevier Science Ltd.

Cite

CITATION STYLE

APA

Bravo, F., Kassou, M., Díaz, Y., & Castillón, S. (2001). Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl-carbohydrate derivatives. Carbohydrate Research, 336(2), 83–97. https://doi.org/10.1016/S0008-6215(01)00256-7

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free