Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.
نویسندگان
چکیده
Gettin' a little sugar-no alcohol required: A procedure for the direct glycosylation of ketones without a hydroxy intermediate enables the site-selective glycosylation of hydroxyketones at the ketone or the alcohol functionality without the use of protecting groups on the aglycone (see scheme). Site selectivity is controlled by the catalyst structure in hydrosilylation and dehydrogenative silylation reactions with sugar silanes. Bn=benzyl.
منابع مشابه
Sugar silanes: versatile reagents for stereocontrolled glycosylation via intramolecular aglycone delivery† †Electronic supplementary information (ESI) available: Experimental details and copies of NMR spectra. See DOI: 10.1039/c5sc00810g
A new method for the intramolecular glycosylation of alcohols is described. Utilizing carbohydrate-derived silanes, the catalytic dehydrogenative silylation of alcohols is followed by intramolecular glycosylation. Appropriate combinations of silane position and protecting groups allow highly selective access to β-manno, α-gluco, or β-gluco stereochemical relationships as well as 2-azido-2-deoxy...
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A new method for the intramolecular glycosylation of alcohols is described. Utilizing carbohydrate-derived silanes, the catalytic dehydrogenative silylation of alcohols is followed by intramolecular glycosylation. Appropriate combinations of silane position and protecting groups allow highly selective access to bmanno, a-gluco, or b-gluco stereochemical relationships as well as 2-azido-2-deoxy-...
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Diorganyl[2-(trimethylsilylethynyl)phenyl]silanes 1a-c and methyl-substituted phenylsilanes 1d and 1e were treated with a small amount of trityl tetrakis(pentafluorophenyl)borate (TPFPB) as an initiator in benzene to afford the corresponding benzosiloles (2a-e) in moderate to good yields. However, no reaction was observed for the reaction using [2-(1-hexynyl)phenyl]diisopropylsilane lf. The met...
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ورودعنوان ژورنال:
- Angewandte Chemie
دوره 48 26 شماره
صفحات -
تاریخ انتشار 2009