Ethyl 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate

T C Baddeley, I G Davidson, J M S Skakle, James Lewis Wardell

Research output: Contribution to journalArticle

Abstract

The crystal structure, at 120 K, and solution H-1 and C-13 NMR spectra of ethyl 1,2,3,4-tetra-O-acetyl-beta-D- glucopyranuronate, (8) have been determined. Compound 8 crystallizes in the triclinic space group, P1(Z = 1) with a = 6.0209(3) Angstrom, b = 8.9698(5) Angstrom, c = 9.9818(8) Angstrom, alpha = 104.965(2)degrees, beta = 98.522(3)degrees, gamma = 106.790(5)degrees. The Cremer and Pople puckering parameters [Q = 0.602(4) Angstrom, theta = 7.1(4)degrees, phi = 325(3)degrees] for the pyranose ring in the solid state indicate a near ideal C-4(1) chair conformation with a slight distortion in the direction towards H-0(5). A number of weak, soft intermolecular C-H...O hydrogen bonds set up a 3D array. NMR spectra and FAB and EIMS data have been obtained. Solution NMR parameters suggest that the solid state conformation is maintained in solution in chloroform.

Original languageEnglish
Pages (from-to)33-38
Number of pages6
JournalJournal of Chemical Crystallography
Volume33
Publication statusPublished - 2003

Keywords

  • glucopyranuronic derivatives
  • conformation
  • NMR
  • MS
  • X-ray-diffraction
  • hydrogen-bond

Cite this

Ethyl 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate. / Baddeley, T C ; Davidson, I G ; Skakle, J M S ; Wardell, James Lewis.

In: Journal of Chemical Crystallography, Vol. 33, 2003, p. 33-38.

Research output: Contribution to journalArticle

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abstract = "The crystal structure, at 120 K, and solution H-1 and C-13 NMR spectra of ethyl 1,2,3,4-tetra-O-acetyl-beta-D- glucopyranuronate, (8) have been determined. Compound 8 crystallizes in the triclinic space group, P1(Z = 1) with a = 6.0209(3) Angstrom, b = 8.9698(5) Angstrom, c = 9.9818(8) Angstrom, alpha = 104.965(2)degrees, beta = 98.522(3)degrees, gamma = 106.790(5)degrees. The Cremer and Pople puckering parameters [Q = 0.602(4) Angstrom, theta = 7.1(4)degrees, phi = 325(3)degrees] for the pyranose ring in the solid state indicate a near ideal C-4(1) chair conformation with a slight distortion in the direction towards H-0(5). A number of weak, soft intermolecular C-H...O hydrogen bonds set up a 3D array. NMR spectra and FAB and EIMS data have been obtained. Solution NMR parameters suggest that the solid state conformation is maintained in solution in chloroform.",
keywords = "glucopyranuronic derivatives, conformation, NMR, MS, X-ray-diffraction, hydrogen-bond",
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T1 - Ethyl 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate

AU - Baddeley, T C

AU - Davidson, I G

AU - Skakle, J M S

AU - Wardell, James Lewis

PY - 2003

Y1 - 2003

N2 - The crystal structure, at 120 K, and solution H-1 and C-13 NMR spectra of ethyl 1,2,3,4-tetra-O-acetyl-beta-D- glucopyranuronate, (8) have been determined. Compound 8 crystallizes in the triclinic space group, P1(Z = 1) with a = 6.0209(3) Angstrom, b = 8.9698(5) Angstrom, c = 9.9818(8) Angstrom, alpha = 104.965(2)degrees, beta = 98.522(3)degrees, gamma = 106.790(5)degrees. The Cremer and Pople puckering parameters [Q = 0.602(4) Angstrom, theta = 7.1(4)degrees, phi = 325(3)degrees] for the pyranose ring in the solid state indicate a near ideal C-4(1) chair conformation with a slight distortion in the direction towards H-0(5). A number of weak, soft intermolecular C-H...O hydrogen bonds set up a 3D array. NMR spectra and FAB and EIMS data have been obtained. Solution NMR parameters suggest that the solid state conformation is maintained in solution in chloroform.

AB - The crystal structure, at 120 K, and solution H-1 and C-13 NMR spectra of ethyl 1,2,3,4-tetra-O-acetyl-beta-D- glucopyranuronate, (8) have been determined. Compound 8 crystallizes in the triclinic space group, P1(Z = 1) with a = 6.0209(3) Angstrom, b = 8.9698(5) Angstrom, c = 9.9818(8) Angstrom, alpha = 104.965(2)degrees, beta = 98.522(3)degrees, gamma = 106.790(5)degrees. The Cremer and Pople puckering parameters [Q = 0.602(4) Angstrom, theta = 7.1(4)degrees, phi = 325(3)degrees] for the pyranose ring in the solid state indicate a near ideal C-4(1) chair conformation with a slight distortion in the direction towards H-0(5). A number of weak, soft intermolecular C-H...O hydrogen bonds set up a 3D array. NMR spectra and FAB and EIMS data have been obtained. Solution NMR parameters suggest that the solid state conformation is maintained in solution in chloroform.

KW - glucopyranuronic derivatives

KW - conformation

KW - NMR

KW - MS

KW - X-ray-diffraction

KW - hydrogen-bond

M3 - Article

VL - 33

SP - 33

EP - 38

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

SN - 1074-1542

ER -