Lewis acid-catalysed rearrangements of Myo-inositol orthoformate derivatives

Ian H. Gilbert, Andrew B. Holmes, Mauricio J. Pestchanker, Rodney C. Young

    Research output: Contribution to journalArticle

    41 Citations (Scopus)

    Abstract

    Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) With di isobytylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-inositol (6). 2,4,5,6-Tetra-O-benzyl-1,3-O-methylene-DL-myo-inositol (16) reacted with allyltrimethylsilane in the presence of Lewis acids to give 2,4,5,6-tetra-0-benzyl-1-O-(3-butenyl)-DL-myo-inositol [(+/-)-17] or rearranged to give 4,5,6-tri-O-benzyl-1,2-0-methylene-DL-myo-inositol [+/-)-18].

    Original languageEnglish
    Pages (from-to)117-130
    Number of pages14
    JournalCarbohydrate Research
    Volume234
    DOIs
    Publication statusPublished - 9 Oct 1992

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