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Tether-directed Radical Cyclization Approaches to the Synthesis of C-Glycosides

6 Tether-directed Radical Cyclization Approaches to the Synthesis of C-Glycosides [Pg.333]

The introduction of an olefin at the anomeric position is synthetically interesting as it permits, via ozonolytic cleavage, access to the anomeric aldehyde, useful for further manipulations. Furthermore, the cleavage of the tether after cyclization releases one hydroxyl group selectively, which may be used chemoselectively in subsequent reactions. This reaction was also shown to be applicable to furanose sugar derivatives [2]. [Pg.334]

Although phenylseleno sugars have been most frequently used as radical precursors, their preparation requires the use of odorous phenylselenol. Furthermore, formation of the anomeric radical usually requires BujSnH, which is also unpleasant to work with. An [Pg.335]




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Approaches to Synthesis

C directed

C-Glycosidation

C-Glycosides

C-glycoside synthesis

C-radicals

Cyclization, of radicals

Cyclizations synthesis

Direct approach

Directed syntheses

Glycoside radical

Glycosides of the

Glycosides synthesis

Glycosidic tethering

Of C-glycosides

Radical cyclization

Radicals synthesis

Synthesis approach

Synthesis cyclization

Synthesis directive

Synthesis of C-glycosides

Synthesis of glycosides

Synthesis of tethered

Tether

Tether-directed radical cyclization

Tethered glycosides

Tethered radical cyclization

Tethering

Tethering Approach

The Directive

The Radical Approach

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