Synthesis, solution and solid-state NMR spectra of methyl 4,6-O-benzylidene-2,3-bis-O-(organostannylmethyl)-a-D-glucopyranosides. Crystal structure of methyl 4,6-O-benzylidene-2,3-bis-O-[(dimethylphenylstannyl)methyl]-a-D-glucopyranoside

S. J. Garden, William Thomas Alexander Harrison, Robert Alan Howie, H. Rufino, J. L. Wardell

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)


Methyl 4,6-O-benzylidene-2,3-bis-O-(PhnMe3-nSnCH2)-alpha -D-glucopyranosides, (3: n = 3; 4: n = 2; 5: n = 1), prepared from methyl 4,6-O-benzylidene-alpha -D-glucopyranoside (6) and PhnMe3-nSnCH2I, contain four co-ordinate tin centres in both solution and solid state. Whereas a single molecular arrangement is indicated in solution for 3-5, evidence for several arrangements in the solid state was obtained for each compound from the Sn-119- and C-13-NMR spectra. An X-ray structure determination of 5 indicated the presence of three slightly differing molecular arrangements, and the absence of any intermolecular contacts. Assignments of the individual Sn signals in the solution NMR spectra of 3 and 5 to their attached CH, groups have been accomplished. The stannacyclic compound, methyl 4,6-O-benzylidene-2,3-bis-O-(2,2-diphenyl-2-stannapropylidene)-alpha -D-glucopyranoside (7) was similarly prepared from 6, using Ph2Sn(CH2I)(2). (C) 2001 Elsevier Science B.V. All rights reserved.

Original languageEnglish
Pages (from-to)226-234
Number of pages8
JournalJournal of Organometallic Chemistry
Publication statusPublished - 2001


  • carbohydrate
  • organotin
  • crystal structures
  • solid-state NMR
  • SN-119


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