- An efficient glycosylation reaction for the synthesis of asialo GM2 analogues
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We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4′-OH of lactose derivatives (3a-d) to synthesiz
- Sun, Bin,Pukin, Aliaksei V.,Visser, Gerben M.,Zuilhof, Han
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p. 7371 - 7374
(2007/10/03)
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- A facile protocol for direct conversion of unprotected sugars into phenyl 4,6-O-benzylidene-per-O-acetylated-1,2-trans-thioglycosides
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A short and practical methodology for conversion of unprotected D-glucose, maltose, cellobiose and lactose into the corresponding phenyl 4,6-O-benzylidine-per-O-acetylated-1,2-trans-thioglycosides is described. The protocol is based on the execution of five reaction steps (bromoacetylation, thiophenolysis under phase transfer catalysis conditions, deacetylation, benzylidenation and acetylation) in one continuous procedure and provides a fast access to the title compounds as pure crystalline products without chromatographic purification.
- Larsen, Kim,Olsen, Carl Erik,Motawia, Mohammed Saddik
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p. 199 - 202
(2007/10/03)
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- Synthesis of a di- and a trisaccharide related to the antigen from Klebsiella type 16
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Using methyl triflate as promoter, methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1 → 4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate) and methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1 → 4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl
- Choudhury, Ambar Kumar,Roy, Nirmolendu
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p. 3937 - 3945
(2007/10/03)
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- Synthesis of ganglioside G(M3) and G(M4) analogs having mimics of ceramide moieties and their binding activities with influenza virus A
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Ganglioside G(M4) (1) and G(M3) (2) analogs, which contain mimics of the ceramide moieties of gangliosides, were synthesized. The syntheses of 1 and 2 feature stereoselective glycosylation of methyl (phenyl 5-acetamido-4,7,8,9- tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-galacto-2-nonulopyranosid)onate (10) as the sialosyl donor with suitably protected galactose and lactose acceptors catalyzed by N-bromosuccinimide (NBS), iodine, and tetrabutylammonium trifluoromethanesulfonate (TBAOTf) as the glycosyl promoter in acetonitrile under kinetically controlled conditions. Compound 2 exhibited binding activity towards influenza virus A.
- Nagao,Nekado,Ikeda,Achiwa
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p. 1536 - 1542
(2007/10/03)
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- Dibutylstannylene acetals: Useful intermediates for the regioselective sulfation of glycosides
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Sulfated mono- and disaccharides were synthesised by a novel sulfation method via regioselective activation of the saccharides to their dibutyltin stannylene acetals, followed by treatment with sulfur trioxide-trimethylamine. This methodology was applied
- Guilbert,Davis,Pearce,Aplin,Flitsch
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p. 2163 - 2178
(2007/10/02)
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- Synthesis of Novel Disaccharides Based on Glycosyltransferases: β1,4Galactosyltransferase
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β1,4Galactosyltransferase and β-galactosidase have been investigated with regard to their acceptor specificity and used in the synthesis of galactosides using 5-thioglucose, deoxyazaglucose, glucal, modified N-acetylglucosamine and glucose derivatives as acceptors.
- Wong, Chi-Huey,Krach, Thomas,Narvor, Christine Gautheron-Le,Ichikawa, Yoshitaka,Look, Gary C.,et al.
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p. 4867 - 4870
(2007/10/02)
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