Glycosyl phosphines

Exploratory Use of Diazirines Formation of Glycosyl Phosphines, Stannanes, N-Sulfonylamines, Esters, Boranes, and Alanes, and of 1,1-Difluorides... 

In 1980, Gross and coworkers first applied this concept to a direct dehydrative glycosylation using tris(dimethylamino)phosphine and carbon tetrachloride [99]. 

Representative Procedure for lodotrimethylsilane and Phosphine Oxide Promoted Clycosylation with Glycosyl Acetate Donors [297]... 

In another approach for the activation of hemiacetals, a phosphine/Cu(II) complex [433] and a rhodium catalyst have been proposed recently [434]. A detailed discussion on the use of hemiacetals in glycosylation reactions can be found in a recent review [435]. 

A second approach relies on the traceless Staudinger ligation between an appropriately functionalized phosphine and an azide to produce a new amide bond [54]. This method has found extensive utility in the labeling of peptides and proteins [215]. Importantly, this method has also been used for the construction of native iV-linked glycans through the reaction between a glycosyl azide and a phosphine containing amino acid [216,217]. 

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