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Synlett 1995; 1995(10): 1069-1070
DOI: 10.1055/s-1995-5155
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[Dimethyl(phenylthiomethyl)silyl]methylmagnesium Chloride. A Novel Hydroxymethylating Reagent

Floris L. van Delft, Gijs A. van der Marel, Jacques H. van Boom*
  • *Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands
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Publikationsdatum:
31. Dezember 2000 (online)

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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