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O-(1-Phenyl-1H-tetrazol-5-yl) Glycosides: Alternative synthesis and transformation into glycosyl fluorides

✍ Scribed by Monica Palme; Andrea Vasella

Publisher: John Wiley and Sons
Year: 1995
Tongue: German
Weight: 761 KB
Volume: 78
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19950780418

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✦ Synopsis

In contrast to the 5-bromo-and 5-iodo-I-phenyl-IN-tetrazoles [7], the fluoro analogue has not been described. The conversion of 5-chloro-l-(phenylrnethyl)-lH-tetrazole to the corresponding fluorotetrazole using K F and [18]crown-6 in MeCN has been reported [8]; however, under these reaction conditions, 5-chloro-1 -phenyl-lH-tetrazole was only partially converted to the corresponding fluorotetrazole, and we obtained inseparable mixtures of the chloro-and fluorotetrazoles (ca. 1 :1, as determined by I3C-NMR).

*) The 'H-NMR data appeared more accurate. Presumably due to the Teflonm liner of the NMR tube, the baselines in the I9F-NMR spectra were not straight.

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