Protecting groups in oligosaccharide synthesis

Protecting Groups in Oligosaccharide Synthesis. Grindley, T. B. In Modem Methods in Carbohydrate Synthesis Khan, Sl H., Oneill, R. A., Eds, Harwood Chur, 1996, pp 225-250. 

Grindley TB (1996) Protecting Groups in Oligosaccharide Synthesis. In Khan SH, O Neill RA (eds) Modern Methods in Carbohydrate Synthesis. Harwood Academic Publishers, Amsterdam, p 225... 

M. Legermiiller, Y. Ito, and T. Ogawa, Use of Dichloropthaloyl (DCPhth) group as amino protection group in oligosaccharide synthesis, Tetrahedron, 54 (1998) 1381-1394. 

Protecting Groups in Oligosaccharide Synthesis Employing Polymer Supports. 111... 

V. PROTECTING GROUPS IN OLIGOSACCHARIDE SYNTHESIS EMPLOYING POLYMER SUPPORTS... 

Hereafter the anomeric center is protected. When the ceramide building block has to be connected to the oligosaccharide, normally selectively deprotection of the C-la position of the lactose is necessary. The thexyldimethylsilyl (TDS) group is a less common trialkylsilyl protecting group in carbohydrate synthesis. Advantageously it survives some rather harsh conditions. The liquid TDSC1 42 with imidazole 43 or DMAP as basic activator in a dipolar aprotic solvent like DMF forms the C-l protected compound 8 as a mixture of anomers.21... 

The Fmoc group is a well-established amino-protecting group [277] often used in peptide synthesis, but only recently has been recognized as a temporary hydroxyl protecting group for oligosaccharide synthesis [277,278,279,280]. 

In particular, the examples given in Schemes 6 and 7 for the application of Dispoke and CDA groups in oligosaccharide synthesis demonstrate magnificently that with these novel protecting groups complex sugars can... 

The selective protection of hydroxyl groups is obviously most frequent in carbohydrate synthesis and, in fact, photosensitive protecting groups have been used to this effect in oligosaccharide synthesis, nucleotide synthesis, and saccharide modification. Here, as well as in other Sections, special attention will be devoted to 2-nitrobenzyl derivatives, whose re-... 

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