Use of (chloromethyl) dimethylphenylsilane in sugar chemistry. Stereo-controlled approach to destomic acid and 1-deoxy-nojirimycin
✍ Scribed by P. Smid; F. J. M. Schipper; H. J. G. Broxterman; G. J. P. H. Boons; G. A. van der Marel; J. H. van Boom
- Book ID
- 104589547
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 525 KB
- Volume
- 112
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
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.