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Synthesis, spectroscopic studies, and x-ray crystallographic analysis of the organotin carbohydrate: 1,2∶3,4-di-O-isopropylidene-6-O-triphenylstannylmethyl-α-D-galactopyranose

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Abstract

The title organotin carbohydrate, C31H36O6Sn, has been synthesized and its molecular structure has been determined in solution and in the solid state. NMR, infrared, mass and X-ray crystallographic techniques were used. The chiral molecules crystallize in the monoclinic space group P21 withZ=2. The triphenyltin and carbohydrate moieties are linked by a trans methylene-oxygen-methylene arrangement. The pyranosyl ring adopts a twist-boat conformation and the isopropylidene rings adopt different (half-chair and envelope) forms. Solution and solid-state conformations are similar as only three Δ13C shift values are greater than 2ppm; the Δ119Sn value is 12 ppm.

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Authors and Affiliations

  1. School of Pharmacy, The Robert Gordon University, AB9 1FR, Schoolhill, Aberdeen, Scotland

    Philip J. Cox & Olga A. Melvin

  2. Department of Chemistry, University of Aberdeen, AB9 2UE, Meston Walk, Old Aberdeen, Scotland

    Simon J. Garden & James L. Wardell

Authors
  1. Philip J. Cox
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  2. Olga A. Melvin
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  3. Simon J. Garden
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  4. James L. Wardell
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Cox, P.J., Melvin, O.A., Garden, S.J. et al. Synthesis, spectroscopic studies, and x-ray crystallographic analysis of the organotin carbohydrate: 1,2∶3,4-di-O-isopropylidene-6-O-triphenylstannylmethyl-α-D-galactopyranose. J Chem Crystallogr 25, 469–475 (1995). https://doi.org/10.1007/BF01665703

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  • DOI: https://doi.org/10.1007/BF01665703

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