Glycosyl phosphates synthesis

Scheme 4 Glycosyl phosphate synthesis from orthoesters...

Synthesis of glycosyl phosphates by exposure of hemiacetals to 81 activated derivatives of phosphoric acid... 

Approaches to the synthesis of glycosyl phosphate diesters as constituents of glycopolymers of the outer membrane of bacteria, yeasts and protozoa and the latest achievements in the field have been profoundly reviewed and will not be covered in this chapter.1,2... 

Synthesis of glycosyl phosphates by activation of the anomeric hydroxyl group... 

Synthesis of glycosyl phosphates by reaction of hemiacetals with activated phosphoric acid derivatives... 

Approaches to glycosyl phosphates based on P(m)-intermediates 4.1 Phosphoramidite approach in the synthesis of glycosyl phosphates... 

Solid-Phase Oligosaccharide Synthesis Using Glycosyl Phosphates... 

Fucosyl phosphate 36 also very efficiently glycosylated the C4 position of acceptor 32. The orthogonality of the activating conditions of thioglycosides and glycosyl phosphate donors was exploited in the synthesis of trisaccharide glycal 41 (Scheme 6.7A).32 Furthermore, the different reactivity of a- and p-glycosyl phosphates was... 

Scheme 6.4 One-pot synthesis of glycosyl phosphates from glycals.

Special Applications of Glycosyl Phosphates in Oligosaccharide Synthesis... 

C-Glycosidic linkages are present in various natural products and may inhibit glycosidases due to the structural analogy to their O-counterparts.42 Glycosyl phosphates 63 and 48 served successfully in the a-selective synthesis of aryl... 

Scheme 6.12 Rearrangement to C-aryl glycosides from aryl O-glycosides following a-selective synthesis using glycosyl phosphates.

Nucleoside 5 -phosphates are employed as starting materials to prepare the activated derivatives (56). Their synthesis has been discussed in a Chapter in this Series.266 The methods used most frequently for preparing glycosyl phosphates involve the interaction of protected glycosyl bromides with diphenyl phosphate and subsequent removal of the protective groups,267 or by fusion of the peracetylated monosaccharides with anhydrous phosphoric acid.268... 

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