Lewis acid-catalysed rearrangements of myo-inositol orthoformate derivatives

Reduction of 2,4,6-tri- O-benzyl- dl- myo-inositol 1,3,5-orthoformate ( 1) with di-isobutylaluminium 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-...

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Published in:Carbohydrate research 1992-01, Vol.234, p.117-130
Main Authors: Gilbert, Ian H., Holmes, Andrew B., Pestchanker, Mauricio J., Young, Rodney C.
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container_title Carbohydrate research
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creator Gilbert, Ian H.
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description Reduction of 2,4,6-tri- O-benzyl- dl- myo-inositol 1,3,5-orthoformate ( 1) with di-isobutylaluminium 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- O-benzyl-1- O-(3-butenyl)- dl- myo-inositol [(±)- 17] or rearranged to give 4,5,6-tri- O-benzyl-1,2- O-methylene- dl- myo-inositol [(±)- 18].
doi_str_mv 10.1016/0008-6215(92)85043-Y
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title Lewis acid-catalysed rearrangements of myo-inositol orthoformate derivatives
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