Li, Sizhe published the artcileStereospecific Synthesis of Glycoside Mimics Through Migita-Kosugi-Stille Cross-Coupling Reactions of Chemically and Configurationally Stable 1-C-Tributylstannyl Iminosugars, Name: (S)-2-Methylpropane-2-sulfinamide, the main research area is iminosugar glycoside mimic stereospecific synthesis; Migita Kosugi Stille coupling configurational stable tributylstannyl iminosugar.
A process for the de novo synthesis of imino-C-glycosides is described. The methodol. is based on the reaction of 1-C-stannylated iminosugars with various electrophiles under the conditions of Migita-Kosugi-Stille cross-couplings, which gives 1-C-substituted iminosugar derivatives in a stereoretentive process. The required iminoglycosyl stannanes are obtained by way of the highly stereoselective addition of tributylstannyllithium to (SR)- or (SS)-N-tert-butanesulfinyl glycosylamines, followed by an activation cyclization sequence. Most interestingly, the methodol. is tunable: the configuration of the tin adduct is controlled exclusively by the tert-butanesulfinyl auxiliary, thus giving access after ring formation to ‘α’-configured or ‘β’-configured iminoglycosyl stannanes. With the subsequent stereoretentive C-C bond-forming process, the methodol. allows the synthesis of pseudo anomers of imino-C-glycosyl compounds in a controlled fashion.
Advanced Synthesis & Catalysis published new progress about Addition reaction. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Name: (S)-2-Methylpropane-2-sulfinamide.
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