Abstract
The synthesis of 2,5-anhydro-3- O-methylsulfonyl-6-thio-1,4-thioanhydro- D-galactitol ( 4; type A structure) and 2,5-anhydro-3,4-di- O-methylsulfonyl-1,6-thioanhydro- D-glucitol ( 10, type B structure), starting from 2,5-anhydro-1,6-dibromo-1,6-dideoxy-3,4-di- O-methylsulfonyl- D-glucitol ( 1) is described. The 4- O-methyl-sulfonyl group of 10 can be displaced by nucleophiles with retention of configuration. In this reaction, a cyclic sulfonium intermediate 21 is involved, which, depending on the nucleophilicity of the anion, leads to different ratios of type A and B compounds. Introduction of a three-membered ring into the 3,4-position of type B compounds yielded tricyclic derivatives of allitol.
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