Kobayashi, Masahiro published the artcileO-glycosylation of 4-(substituted benzyl)-1,2-dihydro-3H-pyrazol-3-one derivatives with 2,3,4,6-tetra-O-acyl-α-D-glucopyranosyl bromide via N1-acetylation of the pyrazole ring, Synthetic Route of 23616-79-7, the publication is Chemical & Pharmaceutical Bulletin (2016), 64(7), 1009-1018, database is CAplus and MEDLINE.
A practical preparation of 4-(substituted benzyl)-3-(2,3,4,6-tetra-O-acyl-β-D-glucopyranosyloxy)-1H-pyrazole derivative is described. O-Glycosylation of 4-(substituted benzyl)-1,2-dihydro-3H-pyrazol-3-one derivative was facilitated by introduction of electron-withdrawing substituents, such as an acetyl group, at the N1-position of the pyrazole ring. 1-Acetyl-4-(substituted benzyl)-1,2-dihydro-3H-pyrazol-3-one reacted with 2,3,4,6-tetra-O-acyl-α-D-glucopyranosyl bromide in the presence of potassium carbonate in acetonitrile to provide the 1-acetyl-4-(substituted benzyl)-3-(2,3,4,6-tetra-O-acyl-β-D-glucopyranosyloxy)-1H-pyrazole derivative in high yield. The synthetic intermediate of Remogliflozin etabonate was synthesized using this strategy.
Chemical & Pharmaceutical Bulletin published new progress about 23616-79-7. 23616-79-7 belongs to chlorides-buliding-blocks, auxiliary class Phase Transfer Catalyst, name is N-Benzyl-N,N-dibutylbutan-1-aminium chloride, and the molecular formula is C19H34ClN, Synthetic Route of 23616-79-7.
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