TY - JOUR
T1 - Use of (chloromethyl) dimethylphenylsilane in sugar chemistry. Stereo‐controlled approach to destomic acid and 1‐deoxy‐nojirimycin
AU - Smid, P.
AU - Schipper, F. J.M.
AU - Broxterman, H. J.G.
AU - Boons, G. J.P.H.
AU - van der Marel, G. A.
AU - van Boom, J. H.
PY - 1993/1/1
Y1 - 1993/1/1
N2 - Addition of [(phenyldimethylsilyl)methyl]magnesium chloride (1d) to 1,2:3,4‐di‐O‐iso‐propylidene‐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.
AB - Addition of [(phenyldimethylsilyl)methyl]magnesium chloride (1d) to 1,2:3,4‐di‐O‐iso‐propylidene‐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.
UR - http://www.scopus.com/inward/record.url?scp=0000601791&partnerID=8YFLogxK
U2 - 10.1002/recl.19931120704
DO - 10.1002/recl.19931120704
M3 - Article
AN - SCOPUS:0000601791
SN - 0165-0513
VL - 112
SP - 451
EP - 456
JO - Recueil des Travaux Chimiques des Pays‐Bas
JF - Recueil des Travaux Chimiques des Pays‐Bas
IS - 7-8
ER -