Concept

Anomer

Related publications (23)

Anomeric effects in pyranosides and related acetals

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

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

Pierre Vogel

A tinglucal tributyl[4,6-O-bis(t-butyl)silylidene-3-O-tris(isopropyl)silyl]tin 7 and a triflate derived from isolevoglucosenone (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate 10 undergo the carbonylative Stille conden ...

2005

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

Syntheses of beta-C(1 -> 3)-Glucopyranosides of 2-and 4-deoxy-D-hexoses

Pierre Vogel, Raynald Demange

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

Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases

Pierre Vogel, Eliazar Rodriguez Garcia

An expeditious and efficient synthesis of new enantiopure polyhydroxylated seven- and eight-membered carbocycles is described starting from 2,3.5-tri-O-benzyl-D-arabinose. The key cyclization step involves ring closing metathesis of 1,8- and 1,9-dienes usi ...

2002

The hetero-Diels-Alder addition of sulfur dioxide to 1-fluorobuta-1,3-dienes: The sofa conformations preferred by 6-fluorosultines (6-fluoro-3,6-dihydro-1,2-oxathiin-2-oxides) enjoy enthalpic and conformational anomeric effects

Pierre Vogel, Rosario Scopelliti

The reactivity of (E)- and (Z)-1-fluorobuta-1,3-diene ((E)- and (Z)-11), 2-fluorobutadiene (12). (E)and (Z)-1-(fluoromethylidene)-2-methylidenecyclohexane ((E)- and (Z)-13) toward SO2 has been explored and compared with that of (Z)- and (E)-1-(fluoromethyl ...

2002

alpha- and beta-homogalactonojirimycins (alpha- and beta-homogalactostatins): Synthesis and further biological evaluation

Pierre Vogel

The homoiminosugars alpha- and beta -homogalactonojirimycins were prepared from a common intermediate, tetra-O-benzyl-D-galacto-heptenitol 6, by way of highly stereoselective reaction sequences involving, as the key steps, an internal amidomercuralion (a-e ...

2001

The C-disaccharide alpha-C(1 -> 3)-mannopyranoside of N-acetylgalactosamine is an inhibitor of glycohydrolases and of human alpha-1,3-fucosyltransferase VI. its epimer alpha-(1 -> 3)-mannopyranoside of N-acetyltalosamine is not

Pierre Vogel, Raynald Demange

The radical C-glycosidation of (-)-(1S,4R,5R,6R)-6-endo-chloro-3-methylidene-5-exo-(phenylseleno)-7-oxa bicyclo[2.2.1]heptan-2-one ((-)-4) with 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl bromide gave (+)-(1S,3R,4R,5R,6R)-6-endo-chloro-5-exo-(phenylselen ...

2000

Rhamnogalacturonan alpha-D-galactopyranosyluronohydrolase - An enzyme that specifically removes the terminal nonreducing galacturonosyl residue in rhamnogalacturonan regions of pectin

A new enzyme, rhamnogalacturonan (RG) alpha-D-galactopyranosyluronohydrolase (RG-galacturonohydrolase), able to release a galacturonic acid residue from the nonreducing end of RG chains but not from homogalacturonan, was purified from an Aspergillus aculea ...

1998

Stereochemical course of hydrolysis catalysed by alpha-L-rhamnosyl and alpha-D-galacturonosyl hydrolases from Aspergillus aculeatus

The stereochemical course of hydrolysis catalysed by four Aspergillus aculeatus enzymes acting on alpha-L-rhamnosyl and alpha-D-galacturonosyl linkages in the hairy regions of pectins has been determined using H-1-NMR. Exogalacturonase acts with inversion ...

1998

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