- Large-scale synthesis of β-L-fucopyranosyl phosphate and the preparation of GDP-β-L-fucose
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A practical 15-mmol large-scale synthesis of β-L-fucopyranosyl dicyclohexylammonium phosphate from L-fucose in 63percent overall yield was developed.The synthesis took advantage of a neighboring Bz-2 group participating in a Koenigs-Knorr like glycosylati
- Adelhorst, Kim,Whitesides, George M.
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- Reliable synthesis of various nucleoside diphosphate glycopyranoses
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A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP-sugars) was developed by using various cycloSal-nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl1-phosphates 2 led to the target NDP-sugars 20-45 in a nucleophilic displacement reaction, which cleaves the cycloSal moiety in anomerically pure forms. As nucleosides cytidine, uridine, thymi-dine, adenosine, 2′-deoxy-guanosine and 2′,3′-dideoxy-2′,3′- didehydrothymidine were used while the phosphates of D-glucose, D-galactose, D-mannose, DNAc-glucosamine, D-NAc-galactosamine, D-fucose, L-fucose as well as 6deoxy-D-gulose were introduced.
- Wolf, Saskia,Zismann, Tanja,Lunau, Nathalie,Meier, Chris
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scheme or table
p. 7656 - 7664
(2010/03/26)
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- Process for the stereoselective preparation of β-fucopyranosyl phosphates and very pure GDP-fucose
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The invention relates to a process for the stereoselective preparation of β-L-fucopyranosyl phosphates via the trichloroacetimidates of protected L-fucose and the synthesis and purification of very pure GDP-fucose from the β-L-fucopyranosyl phosphates.
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- Glycosyl Imidates, 47. Stereospecific Synthesis of α- and β-L-Fucopyranosyl Phosphates and of GDP-Fucose via Trichloroacetimidate
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Reaction of the benzyl- and acetyl-protected α-trichloroacetimidates 1 and 6α with dialkyl and diaryl phosphates in the presence of traces of acid affords stereoselectively the thermodynamically more stable α-L-fucopyranosyl phosphates 2, 7 and 8, respect
- Schmidt, Richard R.,Wegmann, Barbara,Jung, Karl-Heinz
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p. 121 - 124
(2007/10/02)
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