Nucleosides. XXII. Pyrimidine Nucleosides of 4-Amino-4-deoxy-β-D-galactopyranose

概要

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In a four step sequence from 1-O-acetyl-2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-glucose (4), 4′-amino-4′-deoxy-β-D-galactosyl-cytosine (1) was synthesized, involving stannic chloride catalyzed nucleosidation with bis(trimethylsilyl)-N4-acetyl-cytosine, azidolysis of the 4′-sulfonyloxy group, deblocking and reduction (overall yield: 48%). An alternate, though preparatively less satisfactory approach was used for the preparation of the uracil analogue 2, which started from β-D-glucosyl-cytosine or uracil (9 or 15) and proceeded via standard blocking and deblocking reactions to the 4′-O-mesylglucosyl-uracil (20) and was concluded by azidolysis (20, 21), removal of protecting groups and reduction. Structural and configurational assignments evolved from the mode of preparation as well as from spectroscopic data, most conveniently from the acetyl resonances of the peracetylated nucleosides 8 and 24, which are in accord with those of their galactosyl and 3-acetamido-3-deoxy-galactosyl counterparts (Table).
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