152574-30-6Relevant articles and documents
Homologation of protected hexoses with Grignard C1 reagents
Kim, Mikhail,Grzeszczyk, Barbara,Zamojski, Aleksander
, p. 9319 - 9337 (2007/10/03)
Derivatives of three stereoisomeric hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5-8 has been discussed in terms of parallel α- or β-chelated and Felkin-Anh transition states. It has been found that the silyl Grignard reagent 12 exhibits a strong preference for the formation of heptose derivatives of L-configuration at C-6. (C) 2000 Elsevier Science Ltd.
Use of (chloromethyl)dimethylphenylsilane in sugar chemistry. Stereo-controlled approach to destomic acid and 1-deoxy-nojirimycin
Smid, P.,Schipper, F. J. M.,Broxterman, H. J. G.,Boons, G. J. P. H.,Marel, G. A. van der,Boom, J. H. van
, p. 451 - 456 (2007/10/02)
Addition of 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.
