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Synthesis of 2″-oxidized derivatives of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin, and study on structure-chemical shift relationships of urethane(or amide)-type NH protons in synthetic intermediates

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
298
Issue
4
Identifiers
DOI: 10.1016/s0008-6215(96)00318-7
Keywords
  • Dibekacin Derivative
  • Oxo Compound
  • T-Butoxycarbonylamino
  • Amide Proton Shift
  • Inductive Effect
  • Hydrogen Bond
  • Pyridine-D5

Abstract

Abstract Three 2″-modified dibekacin-analogs have been prepared as potential compounds active against resistant bacteria producing 2″- O-phosphotransferases; one is 5-deoxy-5,2″-diepi-5-fluorodibekacin ( 9) prepared from a suitably protected 2″- O-triflyl derivative through the 2″,3″-cyclic carbamate, and the others are 2″-oxo derivatives ( 12 and 22, both as the hydrate) of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin prepared through oxidation at C-2″ of suitably protected derivatives. Relationships between the t-butoxycarbonyl(= Boc)-N H-shifts of per- N-Boc synthetic intermediates and their structures were studied. It was found that the shifts, measured in pyridine- d 5 at 80 °C, which spread over a close range (δ 6–7 ppm), are sensitively influenced by nearby and surrounding groups around the BocNH group in respect of electron-withdrawing character, hydrogen bonding (BocN H … acceptor), and also solvent effects (BocN H … NC 5H 5).

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