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A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of a Heptasaccharide Phytoalexin Elicitor (HPE)

Year: 1997

Type: article

Abstract: A new solid phase method for the synthesis of complex oligosaccharides is described. The method involves attachment to phenolic polystyrene of the first carbohydrate unit, through its anomeric position and via a photolabile linker, using dimethylthiomethylsulfonium triflate as an activator. Reiteration of the glycosidation process allows stereocontrolled growth of linear or branched oligosaccharides in high yield. Cleavage from the resin is efficiently achieved photolytically. The application of the method to the total prepn. of the heptasaccharide phytoalexin elicitor (HPE) is described.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja963482g

Authors: K. C. Nicolaou, Nicolas Winssinger, Joaquín Pastor, Frederik DeRoose

Institutions: Scripps Research Institute, University of California San Diego

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W2019141135

FWCI: 20.35

Cites: 6

Cited by: 231

Related to: 10