Sulfoform generation from an orthogonally protected disaccharide

Abstract

An orthogonally protected disaccharide (GlcN(α1→4)Glc) with a β-linked 2′-aminoethyl linker was used to generate a series of sulfated derivatives (sulfoforms), with a 6-O-sulfate on the glucose residue and one or more sulfate esters on the terminal glucosamine. Deprotection and sulfonation steps were performed in solution and in variable order, with isolated yields of 36–54% (85–90% per operation) after HPLC purification. The modular deprotection–sulfonation sequences can be performed with efficient recovery of the polysulfate products, and avoids complications associated with heterogeneous reactivity in solid-phase synthesis.

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

“…Anti-inflammatory effects (Chung et al, 2012a) Mannosides with hydrophobic substituents TOF Synthesis as DC-SIGN antagonists (Obermajer et al, 2011) 15 N, 13 C 2 8-sialic acid oligomers TOF Evidence for helical structure in a tetramer of 2 8 sialic acid (Battistel et al, 2012) Oligo( -D-glycosyl phosphate) derivatives TOF Use of a phosphoramidite method via boranophosphate intermediates (Fujita et al, 2011b) Orthogonally protected disaccharide MALDI For synthesis of 6-sulfated derivatives with terminal ethylamine (Liu et al, 2012g) Pustulooligosaccharides ( (Yang et al, 2011f) Tri-, penta-, and heptasaccharides, with orthogonally N-protected amino residues TOF Synthesis of four bifunctionalized orthogonally N-protected oligosaccharides derived from lactose and mannose, intended as cross-linking derivatives (Fyrner et al, 2012a) Poly-N-acetyllactosamineextended TOF (DHB) For recognition studies by human and avian influenza A virus hemagglutinins …”

Development of phenylpropanoid sucrose esters as antidiabetic lead compounds

“…Other orthogonal protection schemes for disaccharides were also developed for the synthesis of heparin and heparin sulphate. [105][106][107][108][109][110][111][112] Only two schemes will be discussed in detail as these are the only two schemes that demonstrated full orthogonality of the strategies prior to synthesis of heparin and heparin sulphate. The others failed to demonstrate full orthogonality of their strategies and focused mostly on the synthesis of their desired library of compounds.…”