Synthesis, Structure Characterization, and X-ray Crystallography of Novel 1 -Benzyl-3-phenyl-1H-pyrazole-5-carboxylate Derivatives with a Carbohydrate Moiety

摘要

A series of novel (2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-2i/-pyran-2-yl l-benzyl-3-phenyl-lH-pyrazole-5-carboxylate derivatives (3) were synthesized by the reaction of 2,3,4-tri-O-acetyl-a-D-xylopyranosyl bromide (2) and l-benzyl-3-phenyl-lH-pyrazole-5-carboxylic acid (1) in the presence of sodium bicarbonate and tetrabutylammonium bromide in dichloromethane at reflux temperature. The structures of new compounds were determined by IR and ~1H NMR spectroscopy and HR mass spectrometry (HRMS), and the configuration of the newly generated chiral carbon (C-l) in the xylose ring was tentatively assigned based on the X-ray crystallographic structure of 3d and 3g.