Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates

E R Palmacci; P H Seeberger

doi:10.1021/ol0158462

Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates

Org Lett. 2001 May 17;3(10):1547-50. doi: 10.1021/ol0158462.

Authors

E R Palmacci¹, P H Seeberger

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

PMID: 11388863
DOI: 10.1021/ol0158462

Abstract

[reaction: see text] Mannosyl and glucosyl phosphate donors were successfully used in constructing C-aryl linkages common to many natural products via a Lewis acid induced Fries-like rearrangement. The rearrangement was stereo- and regiospecific, yielding only one C-glycoside product. C-Alkyl glycoside carbohydrate mimetics were generated by using silicon-derived C-nucleophiles and glycosyl phosphates.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Drug Design
Glycosides / chemical synthesis*
Molecular Mimicry
Structure-Activity Relationship

Substances

Glycosides

Grants and funding

1S10RR13886-01/RR/NCRR NIH HHS/United States