208644-75-1Relevant articles and documents
Towards a Synthetic Strategy for the Ten Canonical Carrageenan Oligosaccharides – Synthesis of a Protected γ-Carrageenan Tetrasaccharide
Kinnaert, Christine,Clausen, Mads H.
supporting information, p. 3236 - 3243 (2019/06/08)
Herein, we report a synthetic strategy aiming at synthesizing the ten canonical carrageenan oligosaccharides from one single precursor. The key β-(1→4)-linked disaccharide was synthesized from commercially available galactose pentaacetate. The notoriously difficult formation of β-(1→4)-d-galactan linkages was successfully optimized on the differentially substituted monosaccharides to afford the desired disaccharide in 55 % yield. Following a convergent strategy, two disaccharides were then glycosylated to form the fully protected α-(1→4)-linked tetrasaccharide backbone of the carrageenans. The careful selection of protecting groups provides the opportunity to access all ten carrageenan substructures identified in polysaccharides isolated from red algae. Here, we demonstrate how one such target oligosaccharide can be obtained in a protected form.
Total synthesis of LewisX using a late-stage crystalline intermediate
Munneke, Stefan,Painter, Gavin F.,Gainsford, Graeme J.,Stocker, Bridget L.,Timmer, Mattie S.M.
, p. 1 - 7 (2015/07/15)
Abstract Herein, we report on a highly efficient synthesis of a crystalline protected LewisX trisaccharide that was converted to LewisX following global deprotection. The trisaccharide was prepared in a highly convergent synthesis (seven steps, longest linear sequence) and in a 38% overall yield using a strategy that involved the regioselective glycosylation of a GlcNAc acceptor with a galactose thioglycoside donor, followed by fucosylation of the remaining free GlcNAc hydroxyl as key steps. The core trisaccharide also has the potential to be converted to other members of the Type-2 Lewis family of antigens due to the orthogonal nature of the protecting groups employed.
Nickel(II) chloride-mediated regioselective benzylation and benzoylation of diequatorial vicinal diols
Gangadharmath, Umesh B.,Demchenko, Alexei V.
, p. 2191 - 2193 (2007/10/03)
Ni(II)-chelates of monosaccharide vicinal diols were found to be useful intermediates in regioselective monobenzylation and monobenzoylation. It was observed that the substitution occurs exclusively at the position adjacent to the axially oriented substit