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C(1 -> 4)-linked disaccharides through carbonylative Stille cross-coupling

Publications associées (32)

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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 ...

Wiley-V C H Verlag Gmbh2014

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 ...

2012

Synthesis of C-linked Disaccharides and Analogues as Biomimetics of the TF Epitope

Maria Kolympadi

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 ...

EPFL2011

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 ...

2010

Anomeric effects in pyranosides and related acetals

Pierre Vogel, Sandrine Gerber

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 ...

RCS Publishing2009

Recent Synthetic Approaches Toward Non-anomeric Spiroketals in Natural Products

Pierre Vogel, Sandrine Gerber, Sylvain Favre

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 ...

2008

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 ...

2007

Synthesis of C-glycosides and C-linked disaccharides through carbonylative Stille coupling reactions

Peter Steunenberg

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 ...

EPFL2005

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] ...

2003

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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 ...

2003