C(1 -> 4)-linked disaccharides through carbonylative Stille cross-coupling
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Glycoproteins and glycolipids are major components of the outer surface of mammalian cells. Their carbohydrate moieties, which are directed into the outer environment, serve as ligands for receptor proteins, such as lectins, pathogen proteins and antibodie ...
5-Hydroxymethylfurfural (HMF) is a key platform chemical that may be obtained from various cellulosic (biomass) derivatives. Previously, it has been shown that ionic liquids (ILs) facilitate the catalytic conversion of glucose into HMF. Herein, we demonstr ...
The Oshima-Nozaki (Et2AlI) condensation of isolevoglucosenone (4) with 2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptose (5) gave an enone 6 that was converted with high stereoselectivity to 3-C-[(IR)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl] ...
3,6-Anhydro-1-(aryl or alkylamino)-1-deoxy-D-sorbitol derivatives have been prepared in four steps from isosorbide, a by-product from the starch industry. The inhibitory activities of these new compounds have been evaluated towards 13 glycosidases. A first ...
Sustainably producing concentrated solutions of monosaccharides from biomass is a key challenge facing the conversion of lignocellulosic biomass to biofuels or bioproducts. Most pretreatment and enzymatic hydrolysis processes are run at low-solid concentra ...
The anomeric effect, originally defined as the preference of an electronegative substituent at the anomeric position of pyranosides to stand in an axial rather than an equatorial position, results from the combination of multiple steric, stereoelectronic a ...
Nowadays any natural and non-natural monosaccharide can be prepared pure in both enantiomeric forms starting from inexpensive starting materials. Depending on the target, pure chemical procedures relying upon asymmetric catalysis using either metallic or p ...
Many natural products of biological interest contain [6,5]- and [6,6]-spiroketal moieties that can adopt various configurations, benefiting or not from anomeric conformation stabilizing effects. The spiroketal fragments are often important for the biologic ...
In the first part, we described the synthesis of C-(1'→1) and C-(1'→4) disaccharide precursors, which are readily obtained via the carbonylative Stille coupling of glucal and isolevoglucosenone derivatives. Tin glycals and triflates, derived from isolevogl ...
The influence of substrate compn. on the yield, nature, and compn. of exopolysaccharides (EPS) produced by the food-grade strain G. xylinus I-2281 was investigated during controlled cultivations on mixed substrates contg. acetate and either glucose, sucros ...