Étude structurale d'un C-glycoside insaturé; le tri-O-acétyl-3,4,6-désoxy-2-α-D-thréo-hexéno-2-pyrannosyle benzène

• Published in: Canadian journal of chemistry Vol. 63; no. 2; pp. 491 - 494
• Main Authors: Gillier-Pandraud, Hélène, Brahmi, Rachid, Bellosta-Dechavanne, Véronique, Czernecki, Stanislas
• Format: Journal Article
• Language: English; French
• Published: Ottawa, Canada NRC Research Press 01.02.1985; National Research Council of Canada
• Subjects: Composés hétérocycliques; Composés organiques; Etat condense: structure, proprietes mecaniques et thermiques; Physique; Sciences exactes et technologie; Structure de solides cristallins particuliers; Structure des liquides et des solides; cristallographie; Diffraction RX; Hénéno-2 pyranoside(désoxy-2 phényl-2 tri-O-acétyl-3,4,6); Structure cristalline; Structure moléculaire; Solution chimique; Etude expérimentale; Glycoside; Spectre RMN; Composé organique; Stéréoisomère D-thréo; Hétérocycle oxygène
• ISSN: 0008-4042; 1480-3291
• DOI: 10.1139/v85-079

The structure of 3,4,6-tri-O-acetyl-2-deoxy-α- D -threo-hexeno-pyranosyl benzene 1 has been determined by X-ray diffraction methods. Crystals of 1 are orthorhombic, space group P2 1 2 1 2 1 with a = 22.946(10), b = 10.319(6), c = 7.684(4) Å, V = 1819.42 Å 3 , Z = 4, ρ c  = 1.27 g cm −3 . The sugar moiety exhibits a half-chair 0 H 5 conformation in which the aromatic ring is quasi-axial. The anomeric carbon has the α. configuration. The comparison of the 1 H nmr data with the crystallographic data established that, in solution, the conformation of 1 is very similar to that in the crystalline state.