P. Smid et al., USE OF (CHLOROMETHYL)DIMETHYLPHENYLSILANE IN SUGAR CHEMISTRY - STEREO-CONTROLLED APPROACH TO DESTOMIC ACID AND 1-DEOXY-NOJIRIMYCIN, Recueil des travaux chimiques des Pays-Bas, 112(7-8), 1993, pp. 451-456
Addition of [(phenyldimethylsilyl)methyl]magnesium chloride (1d) to op
ylidene-alpha-D-galacto-hexodialdo-1,5-pyranose, and further processin
g of the resulting anti-alpha-hydroxy-silane adduct by a well-establis
hed sequence of reactions, gives a precursor to destomic acid 2. Simil
arly, addition of the Grignard reagent Id to opropylidene-alpha-D-xylo
-pentodialdo-1,4-furanose proceeds with a high degree of stereoselecti
vity to give, after further elaboration of the syn-alpha-hydroxy-silan
e adduct, the antibiotic 1-deoxynojirimycin.