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Preparation and conformation of α-l-arabinofuranosyl-pyridinium salts, and hydrolysis of the 4-bromoisoquinolinium compound

✍ Scribed by Michael L. Sinnott; W.S.Sulochana Wijesundera

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 783 KB
Volume: 136
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)85209-5

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✦ Synopsis

Tri-0-benzoyl-cu-L-arabinofuranosylpyridinium salts can be made in acceptable yields and high stereochemical purity by the reaction of 2,3,5-tri-O-benzoyl-a-L-arabinofuranosyl bromide and the pyridine in the presence of tetrabutylammonium bromide. Analysis of the 'H-n.m.r. signals of the sugar reveals that the benzoylated compounds adopt largely the E, conformation whereas the debenzoylated compounds are largely in the oT, conformation. The a-L-arabinofuranosyl-4bromoisoquinolinium ion hydrolyses by both pH-independent and base-catalysed pathways, complicated by the reversible formation of an inert pseudo-base in alkali. The comparatively low rate of the pH-independent reaction is discussed in terms of the acid-lability of furanosides.

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