USE OF (CHLOROMETHYL)DIMETHYLPHENYLSILANE IN SUGAR CHEMISTRY - STEREO-CONTROLLED APPROACH TO DESTOMIC ACID AND 1-DEOXY-NOJIRIMYCIN

Authors
SMID P SCHIPPER FJM BROXTERMAN HJG BOONS GJPH VANDERMAREL GA VANBOOM JH
Citation
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
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Recueil des travaux chimiques des Pays-Bas → ACNP
ISSN journal
01650513
Volume
112
Issue
7-8
Year of publication
1993
Pages
451 - 456
Database
ISI
SICI code
0165-0513(1993)112:7-8<451:UO(ISC>2.0.ZU;2-F
Abstract
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.