Regio‐ and stereoselective iodinations under controlled Garegg conditions were performed on vicinal diols and contiguous triols located on pyranose templates. β‐ D ‐Fructo‐ orpsicopyranose‐based diols were selectively iodinated at C‐5 or C‐4, respectively, to afford the L ‐ sorbo or D ‐tagato iodohydrins. In contrast, the related triols only underwent selective iodination at C‐5. Application of the process to D ‐gluco‐ and D ‐galactopyranosides resulted in selective iodination at C‐3 or C‐4, respectively, to afford the D ‐ allo or D ‐ gluco iodohydrins.
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Simao et al. (2011) studied this question.
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