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

    Cite this

    Gilbert, Ian H. ; Holmes, Andrew B. ; Pestchanker, Mauricio J. ; Young, Rodney C. . / Lewis acid-catalysed rearrangements of Myo-inositol orthoformate derivatives. In: Carbohydrate Research. 1992 ; Vol. 234. pp. 117-130.
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    title = "Lewis acid-catalysed rearrangements of Myo-inositol orthoformate derivatives",
    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].",
    author = "Gilbert, {Ian H.} and Holmes, {Andrew B.} and Pestchanker, {Mauricio J.} and Young, {Rodney C.}",
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    Lewis acid-catalysed rearrangements of Myo-inositol orthoformate derivatives. / Gilbert, Ian H.; Holmes, Andrew B. ; Pestchanker, Mauricio J. ; Young, Rodney C. .

    In: Carbohydrate Research, Vol. 234, 09.10.1992, p. 117-130.

    Research output: Contribution to journalArticle

    TY - JOUR

    T1 - Lewis acid-catalysed rearrangements of Myo-inositol orthoformate derivatives

    AU - Gilbert, Ian H.

    AU - Holmes, Andrew B.

    AU - Pestchanker, Mauricio J.

    AU - Young, Rodney C.

    PY - 1992/10/9

    Y1 - 1992/10/9

    N2 - 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].

    AB - 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].

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