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Synlett 1995; 1995(10): 1069-1070
DOI: 10.1055/s-1995-5155
DOI: 10.1055/s-1995-5155
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[Dimethyl(phenylthiomethyl)silyl]methylmagnesium Chloride. A Novel Hydroxymethylating Reagent
Further Information
Publication History
Publication Date:
31 December 2000 (online)
The readily accessible hydroxymethylating reagent [dimethyl(phenylthiomethyl)silyl]methylmagnesium chloride (1c) adds to sugar aldehyde 2 with high stereoselectivity to give stable syn-adduct 3c, the C-Si bond of which is cleaved under mild oxidative conditions, resulting in the L-glycero-D-manno-heptopyranoside derivative 4.
hydroxymethylation - LD-Hepp - dimethyl(phenylthiomethyl)silyl group - sila-Pummerer