Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)2/HgBr2/TMSCN

Authors

Andreas H. Franz, University of the PacificFollow
YiQiu Wei, University of the Pacific
Vyacheslav V. Samoshin, University of the PacificFollow
Paul H. Gross, University of the PacificFollow

Document Type

Article

Publication Title

Journal of Organic Chemistry

Department

Chemistry

ISSN

0022-3263

Volume

67

Issue

22

DOI

10.1021/jo0111661

First Page

7662

Last Page

7669

Publication Date

10-8-2002

Abstract

Lewis acid-catalyzed dimerization of mono- and disaccharidic per-O-acetylated glycals gave di- and tetrasaccharidic O-acetylated C-glycosides, respectively. 2,3-Enopyranosyl cyanides were obtained from per-O-acetylated glycals by a new, mild anomeric SN‘-acetoxy displacement with Hg(CN)2/HgBr2/TMSCN. Per-O-acetylated 2-C-2-deoxy-pyranoses were converted into pyranosyl cyanides by the same reagent. An unprecedented acetic acid elimination from dimers with d-galacto- and l-fuco-configurations accompanied the SN-displacement under those conditions. A new set of 1H NMR coupling constants for 2,3-enopyranosyl systems was used for configurational assignment of complicated tetrasaccharide mimics.

Recommended Citation

Franz, A. H., Wei, Y., Samoshin, V. V., & Gross, P. H. (2002). Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)2/HgBr2/TMSCN. Journal of Organic Chemistry, 67(22), 7662–7669. DOI: 10.1021/jo0111661
https://scholarlycommons.pacific.edu/cop-facarticles/141