Conformational restriction by intramolecular hydrogen bonding. Carbohydrate-carbohydrate self-assembly

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1659-1662

  De La Paz, Manuela López ^a   Ellis, Gary ^b   Penadés, Soledad ^a   Vicent, Cristina ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE CIENCIA Y TECNOLOGÍA DE POLÍMEROS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CONFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0031550859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00156-1     Document Type: Article

References (45)

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29. 19. These epoxides have been opened with sodium azide to give the corresponding 3-azide derivative (90%). By reduction with lithium aluminum hydride, 3-amine-1,6-anhydro-3-deoxy-2,4-dibenzyl-β-D-glucopyranoside was obtained (86%). All new products gave satisfactory spectroscopic data and elementary analysis.
30. Py (cis-out), and one cis-one trans (trans).
31. 11. Molecular Mechanics Calculations were carried out using MM2* according to the GB/SA solvent model for chloroform. Initially, 9 structures were calculated for each rotamer (cis-in, cis-out, trans) by rotating the torsion around the N-C3 bond. The structure generation was performed maintaining the OH in a fixed orientation.
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42. -1 on a (Perkin Elmer System 200 FT-IR) equipped with a DTGS detector, in a 0.1 mm fixed pathlength liquid cell fitted with the solvent in the cell. The absorbance scale in the figure 1 is normalized for each compound. (Nicolet 520B FT-IR spectrometer)
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44. -1. We thank Dr. C. A. Hunter (University of Sheffield) for kindly providing the fitting program.
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