Use of (chloromethyl)dimethylphenylsilane in sugar chemistry. Stereo-controlled approach to destomic acid and 1-deoxy-nojirimycin

Article abstract of DOI:10.1002/recl.19931120704

Addition of <(phenyldimethylsilyl)methyl>magnesium chloride (1d) to 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose, and further processing of the resulting anti-α-hydroxy-silane adduct by a well-established sequence of reactions, gives a precursor to destomic acid 2.Similarly, addition of the Grignard reagent 1d to 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose proceeds with a high degree of stereoselectivity to give, after further elaboration of the syn-α-hydroxy-silane adduct, the antibiotic 1-deoxynojirimycin.