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- W2952678093 abstract "Treatment of phenyl 1-thio- and allyl 2,6-di-O-benzoyl-D-galactopyranosides 3 with methyl pyruvate and BF3 · Et2O in various solvents gave 1,6-anhydro-3,4-di-O-benzoyl-2-deoxy-2-phenylthio-β-D-idopyranose (4) and the corresponding diastereomers of 3,4-O-pyruvate acetal-containing galactosides 5. The phenyl 1-thio-β-galactoside R-5a and the allyl a-galactoside R-5b were both converted into methyl 3,4-O-[1-(R)-(methoxycarbonyl)ethylidene]-β-D-galactopyranoside (9), the structure of which as well as that of 4 was confirmed by X-ray crystallography. Compound R-5a was converted into 5-[(benzyloxycarbonyl)amino]pentyl 6-O-benzoyl-3,4-O-[1-(R)-(methoxycarbonyl)ethylidene]-β-D-galactopyranoside (18) by using the (2-chloroacetoxymethyl)benzoyl (CAMB) group for the temporary protection of position 2. Glucosamination of 18 and subsequent deblocking of the intermediate disaccharide gave β-D-GlcpNAc-(1→2)-3,4-(S)-pyruvate-β-D-Galp-O(CH2)5NH2 (21) which represents a fragment of the Escherichia coli K 47 polysaccharide." @default.
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- W2952678093 date "1994-09-02" @default.
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- W2952678093 title "Preparation of Diastereomeric 3,4-O-Pyruvate Acetal-ContainingD-Galactopyranose Derivatives, Structural Assignment and Use for Oligosaccharide Synthesis" @default.
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- W2952678093 doi "https://doi.org/10.1002/jlac.199419940903" @default.
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