Phenylsulfenyl glycosyl donors

The application of thioglycoside gained a new impetus by the finding of Kahne et al. [56] who observed that phenylsulfenyl glycosyl donors, readily accessible by oxidation (/mCPBA) of phenyl thioglycosides, can be effectively glycosylated using... 

Originally, the iV-trifluoroacetyl (TFAc) derivative of sialic acid was introduced by Bovins and co-workers as a 2-bromide glycosyl donor, which was reacted with benzyl alcohol in the presence of sym-collidine to give a 1/2 mixture of a- and -glycosides in 30% yield [16]. In our laboratory, the 2-phenylsulfenyl derivative of A-TFAc sialic acid has been used for the synthesis of de-A-acetyl-6-sulfo-sialyl Lewis X [97]. However, Boons and co-workers were again first to describe the high potential of the A-TFAc sialyl donor [98]. 

SUva, D. et al.. Stereospecific solution- and solid-phase glycosylations. Synthesis of P-linked saccharides and constrnction of disaccharide libraries using phenylsulfenyl 2-deoxy-2-triflnoroacetamido glycopyranosides as glycosyl donors, J. Org. Chem., 64, 5926, 1999. 

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