Derivatives of enose-and ynosephosphonates and related compoundsPreliminary communication
SummaryThe gem-dibromo terminal enoses 1 and 7 are convenient sources of glycosylacetylenes which upon reaction with phosphorus electrophiles gave the phosphorusbearing acetylenic sugars 4, 5 and 8. Compounds 5 and 8 underwent cycloaddition reactions leading to isoxazolyl-C-glycosides 6 and 9 respectively. The nitroolefinic sugar derivative 11 gave upon bromination-dehydrobromination the first example of a new kind of potentially useful synthetic intermediates, the gem-bromonitroenose 12. The enosephosphonate 13 was also prepared from 111. The diglycosylhydroxylamine 18 represents another type of phosphorus-bearing acetylenic sugar derivative. Some 'H-and 13C-NMR. data relative to the new tylpes of phosphoruscontaining sugar derivatives synthesized are given.L'activitt anticancereuse de certains accepteurs de Michaei' derivts de sucres [2], de m&me que l'inter&t biologique potentiel de sucres phosphorts qui, de plus, constituent des modeles particulithement riches pour l'ttude par RMN. de couplages a longue distance 31P, l3C et 31P, 'H, nous a amene a prkparer quelques dialkoxyphosphinylenoses et dialkoxyphosphinylynoses ainsi lque des composes apparentes. Nous montrerons ultCrieurement que certains des nouveaux types de dtrives de sucres dkcrits ci-dessous3) sont des intermtdiaires de synthese tres riches.La phosphine 4 (sirop, Sucres phosphores 111; 11: 111. Une communication plus detaillee paraitra ulteneurement. Les analyses dementaires et les donntes spectroscopiques (UV., IR., RMN., SM.) de tous les nouveaux composCs decrits sont en accord avec la structure proposee.[
The aldehydes (II) are transformed via the intermediates shown in the scheme into the title compounds (VI) [the anomer (VII) is formed in addition to (VId); the nitroenoses (Vc), Vd) are known compounds].
Es werden Wege zur Synthese von Desoxyhydroxy‐aminozuckern, wie z.B. (II), (IV), (V) [über (V) lassen sich Glykopeptid‐ Bindungen eines neuen Typs knüpfen, wie sie das Nitron (VI) aufweist], (VIII), (IX), (XI), (XIII) und (XVI), aufgezeigt (keine eingehenderen Darstellungsvorschriften), die eine strukturelle Verwandtschaft zu bestimmten biochemisch wichtigen Molekülen haben.
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