TY - JOUR
T1 - 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
AU - Garden, S. J.
AU - Harrison, William Thomas Alexander
AU - Howie, Robert Alan
AU - Rufino, H.
AU - Wardell, J. L.
PY - 2001
Y1 - 2001
N2 - 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.
AB - 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.
KW - carbohydrate
KW - organotin
KW - crystal structures
KW - solid-state NMR
KW - RAY-DIFFRACTION ANALYSIS
KW - MOLECULAR-STRUCTURE
KW - DERIVATIVES
KW - SN-119
U2 - 10.1016/S0022-328X(00)00678-1
DO - 10.1016/S0022-328X(00)00678-1
M3 - Article
SN - 0022-328X
VL - 619
SP - 226
EP - 234
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
ER -