Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2003 Dec 26;68(26):10152-5.
doi: 10.1021/jo0350256.

Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide

Jason L McCartney  1 , Christopher T Meta, Robert M Cicchillo, Matthew D Bernardina, Timothy R Wagner, Peter Norris
Affiliations

Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide

Jason L McCartney et al. J Org Chem. .

Abstract

Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a d-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.

PubMed Disclaimer

Publication types

LinkOut - more resources