154920-28-2Relevant articles and documents
Modular synthesis of heparin oligosaccharides
Orgueira, Hernan A.,Bartolozzi, Alessandra,Schell, Peter,Litjens, Remy E. J. N.,Palmacci, Emma R.,Seeberger, Peter H.
, p. 140 - 169 (2007/10/03)
A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were uti
Solid- and solution-phase synthesis of heparin and other glycosaminoglycans
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, (2008/06/13)
Described is a modular, general synthetic strategy for the preparation in solution and on a solid support of heparin, heparin-like glycosaminoglycans, glycosaminoglycans and non-natural analogs of each of them. Additionally, the modular strategy provides
Attempted synthesis of type-A inositolphosphoglycan mediators - Synthesis of a pseudohexasaccharide precursor
Martin-Lomas, Manuel,Flores-Mosquera, Maria,Chiara, Jose Luis
, p. 1547 - 1562 (2007/10/03)
A block synthesis approach to the inositol-containing pseudohexasaccharide 1 is presented. The myo-inositol building block 6 has been prepared using a key regioselective acylation through a boron-tin exchange reaction and the 2-azido-2-deoxy glycosyl donors 15 and 17 have been synthesized from D-glucosamine using a diazo transfer reaction. The anomeric position of the mono- and disaccharide building blocks has been temporarily protected as phenyl thioglycoside and this function was then converted into the different leaving groups to perform the glycosylation reactions. Both trichloroacetimidates and fluorides have been used as glycosyl donors for the construction of the different glycosidic linkages. The protected pseudohexasaccharides 44, 48-50, which are precursors of pseudohexasaccharide 1, have been efficiently prepared and fully characterized. Pseudohexasaccharide 1 contains the fundamental structural features which have been proposed for type A inositolphosphoglycans, which may be involved in the insulin-signaling process.
Dispiroketals in synthesis (part 5): A new opportunity for oligosaccharide synthesis using differentially activated glycosyl donors and acceptors
Boons, Geert-Jan,Grice, Peter,Leslie, Ray,Ley, Steven V.,Yeung, Lam Lung
, p. 8523 - 8526 (2007/10/02)
The reactivity of dispiroketal protected thioglycosides makes them useful new precursors for oligosaccharide synthesis as is illustrated by the preparation of a protected pentasaccharide unit common to the variant surface glycoprotein of Trypanosoma bruce