Publication

Convergent syntheses of C(1 -> 3)-linked disaccharides starting from isolevoglucosenone

Pierre Vogel
2000
Journal Articles

Abstract

Nucleophilic addition (Nu-Mf) to isolevoglucosenone 1 generates enolates stereospecifically (exo face addition) that can be reacted with sugar-derived aldehydes to give C(1-->3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et2AlI as the nucleophile. This leads to products of Baylis-Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-beta -D-gulo-pyranose 5. (C) 2000 Elsevier Science Ltd. All rights reserved.

Official source

https://infoscience.epfl.ch/entities/publication/d43f82cf-2350-43e3-b346-700b0e4464f1

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Pierre Vogel
2000
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/d43f82cf-2350-43e3-b346-700b0e4464f1

About this result

Related concepts (2)

Carrageenan

Carrageenans or carrageenins (ˌkærəˈɡiːnənz ; ) are a family of natural linear sulfated polysaccharides that are extracted from red edible seaweeds. Carrageenans are widely used in the food industry, for their gelling, thickening, and stabilizing properties. Their main application is in dairy and meat products, due to their strong binding to food proteins. In recent years, carrageenans have emerged as a promising candidate in tissue engineering and regenerative medicine applications as they resemble native glycosaminoglycans (GAGs).

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Cellulose is an organic compound with the formula (C6H10O5)n, a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall of green plants, many forms of algae and the oomycetes. Some species of bacteria secrete it to form biofilms. Cellulose is the most abundant organic polymer on Earth. The cellulose content of cotton fiber is 90%, that of wood is 40–50%, and that of dried hemp is approximately 57%.