English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Highly selective metal-graphite-induced reductions of deoxy halo sugars

MPS-Authors
There are no MPG-Authors available
External Resource
No external resources are shared
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
Citation

Fürstner, A., & Weidmann, H. (1989). Highly selective metal-graphite-induced reductions of deoxy halo sugars. The Journal of Organic Chemistry, 54(10), 2307-2311. doi:10.1021/jo00271a012.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0010-25D8-C
Abstract
To explore the applicability of highly active metal-graphite reducing agents to polyfunctional compounds a variety of suitably protected chloro-, bromodeoxy- and deoxyiodohexopyranosides and hexofuranoses were each treated with potassium-graphite laminate (C8K) and zinc/silver-graphite, respectively, invariably leading to the efficient formation of olefinic products. However, while C8K in all cases causes dehydrohalogenation, zinc/silver-graphite reductions proceeded by dealkoxyhalogenation, results quite opposite to the formation of glycals by each of the reagents. In contrast, magnesium on graphite readily dimerizes Me 6-deoxy-6-iodo-α-D-glucopyranoside by a Wurtz reaction.