Glycoside synthesis orthogonal

Glycomimetics, 468 Glycoproteins, biosynthesis, 486, 487 Glycosidases, 487, 491, 492 Glycoside synthesis, 381 anomeric selectivity, 382 challenges, 382 via electrochemistry, 385 via electron transfer, 385 inductive effects, 452 miscellaneous methods, 432 new glycosyl donors, 386 orthogonal, 452 overview, 381... 

This observation created a solid basis for the evaluation of the STaz glycosides in orthogonal glycosylations in combination with S-ethyl glycosides. The promoter of choice for this synthesis would be AgOTf for the STaz activation, under which conditions the SEt moiety is entirely stable. Conversely, it should be possible to activate SEt in the presence of NIS and catalytic TfDH, conditions under which the STaz moiety remains stable. This concept was demonstrated by synthesizing the trisaccharide 57 via two strategically different approaches. 

P. Pomsuriyasak and A. V. Demchenko, S-Thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis, Chem. Eur. J., 12 (2006) 6630-6646. 

A. V. Demchenko and C. De Meo, semi-Orthogonality of O-pentenyl and S-ethyl glycosides Application for the oligosaccharide synthesis, Tetrahedron Lett., 43 (2002) 8819-8822. 

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