Orthogonal oligosaccharide synthesis

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. 

T. Ako, S. Daikoku, I. Ohtsuka, R. Kato, and O. Kanie, A method of orthogonal oligosaccharide synthesis leading to a combinatorial library based on stationary solid-phase reaction, Chem. Asian J., 1 (2006) 798-813. 

An interesting, new strategy which can also be used for an orthogonal oligosaccharide synthesis has been developed by Boons. 

Scheme 4.86 Orthogonal thioimidate-based, one-pot oligosaccharide synthesis [468].

Another hybrid protecting group is the p-[(trimethylsilyl)ethoxy]methoxy benzyl (p-SEM-benzyl) ether354 Phenolate anions generated by treatment of p-SEM-benzyl ethers with TBAF in DMF at 80 °C eliminate to give the deprotected alcohol as illustrated in Scheme 4.303 p-SEM-benzyl ethers are compatible with many of the standard manipulations in oligosaccharide synthesis and they arc orthogonal to benzyl and p-methoxybenzyl ethers. 

The combination of two chemically distinct glycosylation reactions, in which one of the leaving groups is activated while the other one remains intact, and vice versa, has led to the discovery of the orthogonal strategy for oligosaccharide synthesis.4... 

H. Paulsen, Progress in oligosaccharide synthesis through a new orthogonal glycosylation strategy,... 

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. 

Progress in Oligosaccharide Synthesis through a New Orthogonal Glycosylation Strategy... 

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