C(1 -> 4)-linked disaccharides through carbonylative Stille cross-coupling
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Radical C-glycosidation of racemic 5-exo-benzeneselenyl-6-endo-chloro-3-methylidene-7-oxabicyclo[2.2.1]hept an-2-one ((+/-)-2) with alpha -acetobromofucose (3) provided a mixture of alpha -C-fucosides that were reduced with NaBH4 to give two diastereomeric ...
Disaccharide and oligosaccharide mimics are potentially more selective glycosidases inhibitors than simple monosaccharide mimics. They represent also more selective ligands for lectins and oligosaccharide receptors and can become immunostimulating agents. ...
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 ...
Intercellular communication is governed by interactions between surface oligosaccharides and glycoproteins. The biosynthesis of these molecules involves glycosidations catalyzed by glycosyltransferases and hydrolysis of O-glycosyl linkages catalyzed by gly ...
The ''naked sugar'' (+)-1 (1R,2S,4R)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1S')-camphanate) has been converted into (+)-(1R,4R,5R,6R)-3-methylidene-5-exo,6-exo(isopropylidenedioxy)-7-oxabi cyclo[2.2.1]heptan-2-one ((+)-3) and (-)-(1S,4R,5R,6R)-5-exo-( ...
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 ...
A (-)-conduritol F derivative was condensed with 4-ethyl-7-hydroxy-2H-1-benzopyran-2-one and converted into (+)-4-ethyl-7-[( 1'R,2'S,3'S,4'R)-2',3',4'-trihydroxycyclohexyloxy]-2H-1benzopyran-2-one ((+)-2) Enantiomer (-)-2 was obtained from a (+)-conduritol ...
(1R,2R,4R)-2-exo-Cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1S')-camphanate [(+)-1, Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate] was transformed with high stereoselectivity into (1R,2R,6R,7R)-4-phenyl-3,10-dioxa-5-azatricyclo[5.2.1.0(2,6)]dec ...
The Diels-Alder adduct (+)-l of furan to 1-cyanovinyl (1'S)-camphanate was converted to methyl 3,5-O-diacetyl-2,6-dideoxy-beta-L-lyxo-hexofurano-side ((+)-12), a protected form of 2-deoxy-L-fucose, in 8 steps and 16.6% overall yield. ...
The alpha-(1-->3)- and alpha-(1-->4)-linked C-disaccharides derived from D-glucose and L-mannose have been obtained with high stereoselectivity via the addition of 2,3,4,6-tetra-O-acetyl-glucopyranosyl radical to (1S,4R,5R,6R)-6-endo-chloro-3-methylidene-5 ...
