Synthesis of new sulfonic acid-containing oligosaccharide mimetics of sialyl Lewis A

Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate

“…The reaction required low power microwave irradiation, probably because the axial disposition of HO-3 lessens its reactivity as described for gulo-configured derivatives. 41 On the other hand, surprisingly, compound 2 and its triflate 3 had the same chromatographic mobility in a number of solvents, a fact that complicated the analysis. The 1 H-NMR spectrum of 3 showed that H-3 appeared strongly deshielded at 5.39 ppm.…”

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2009–2010

“…Trisaccharide. Neu5Ac and Fuc replaced with HSO 3 and D-Ara respectivly (Jakab et al, 2010) Pentasaccharide anticoagulant (Idraparinux) MALDI Compound is fully O-sulfated, O-Me mimic of antithrombin III binding domain of heparin ) N-Quaternary chitosan derivatives TOF Synthesis, characterization and antibacterial activity (Rúnarsson et al, 2010) Sialylated lactosides TOF (DHB), per-Me For coupling to BSA by Huisgen reaction. As glycocongugate antigen (Mosley et al, 2010) Sialyllacto-N-tetraose and sialyllacto-N-neotetraose TOF Use of α2-3and α2-6-sialylated lactosaminide precursors obtained by enzymatic procedures with glycosylations employing triflic acid/N-iodosuccinimide (Schmidt & Thiem, 2010) Sucrose-based guanidinecontaining G7 molecular transporters TOF Show different patterns of intracellular localization depending on the nature of the linker chains as well as the fluorescent dyes (Lee et al, 2009l) Sulfated oligofucosides MALDI Synthesis of sulfated octyl tetra-to octaoligofucosides with different sulfation patterns (Zong et al, 2010a) α…”

A Journey into Recent Microwave‐Assisted Carbohydrate Chemistry

“…Borbàs and co-workers [62] synthesized two trisaccharides as new sulfonic acid analogs of sialyl Lewis acids by employing low-power MWI for the efficient and complete formation of the gulo-triflate derivatives, while the synthesis of the galacto-triflates took place smoothly by CH.…”