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 journalArticle

1 Citation (Scopus)

Abstract

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
Volume619
DOIs
Publication statusPublished - 2001

Keywords

  • carbohydrate
  • organotin
  • crystal structures
  • solid-state NMR
  • RAY-DIFFRACTION ANALYSIS
  • MOLECULAR-STRUCTURE
  • DERIVATIVES
  • SN-119

Cite this

@article{256602a0689648c8822c2cba6599cf43,
title = "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",
abstract = "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.",
keywords = "carbohydrate, organotin, crystal structures, solid-state NMR, RAY-DIFFRACTION ANALYSIS, MOLECULAR-STRUCTURE, DERIVATIVES, SN-119",
author = "Garden, {S. J.} and Harrison, {William Thomas Alexander} and Howie, {Robert Alan} and H. Rufino and Wardell, {J. L.}",
year = "2001",
doi = "10.1016/S0022-328X(00)00678-1",
language = "English",
volume = "619",
pages = "226--234",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

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

VL - 619

SP - 226

EP - 234

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -