Sulfonate protecting groups. Regioselective O -sulfonylation of myo -inositol orthoesters

Sureshan, Kana M ; Shashidhar, Mysore S (2001) Sulfonate protecting groups. Regioselective O -sulfonylation of myo -inositol orthoesters Tetrahedron Letters, 42 (16). pp. 3037-3039. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/S0040-4039(01)00364-1

Related URL: http://dx.doi.org/10.1016/S0040-4039(01)00364-1

Abstract

Sulfonylation of myo-inositol 1,3,5-orthoesters with alkyl or aryl sulfonyl chlorides in the presence of sodium hydride gives the corresponding 4,6-di-O-sulfonates in good yields. These sulfonates can be cleaved with magnesium in methanol to generate the free myo-inositol derivative. This methodology was used for the preparation of racemic 2,4-di-O-benzyl-myo-inositol and 2-O-benzyl-myo-inositol, which are precursors for some phosphoinositols.

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