✦ LIBER ✦

First preparation of pyranosid nitroolefin having a peroxy group and its reaction with some nucleophiles

✍ Scribed by Akinori Seta; Kiyohisa Tokuda; Tohru Sakakibara

Publisher: Elsevier Science
Year: 1993
Tongue: French
Weight: 122 KB
Volume: 34
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)79175-1

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✦ Synopsis

Treatment of nitroalkene I with t-butyl hydroperoxide and m-chloroperbenzoic acid gave the SIG?' product and 2,3-anhy&o derivative, respectively, in high yields. The former product is proved fo be usefur intermediate for introduction of nucleophiles at C-4.

To our best knowledge, there is no sport for preparation of nitm sugars having a reactive peroxy group. In general the reactions of niWenes with peroxi& such as t-butyl hydroperoxide give the nitro epoxide for its facile cleavage of the O-O bond.1 Assuming that the reaction between a hydmperoxide and nitroalkene having a gocd leaving group at the p-position affords the SN~' product, we have performed the reaction of 1 with r-bury1 hydroperoxide and indeed obtained the intending peroxy product 4 in high yield.

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