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X-ray analysis of 3-O-(6-O-acetyl-2,4-diazido-3-O-benzyl-2,4-dideoxy-α-d-glucopyranosyl)-1,6-anhydro-2,4-diazido-2,4-dideoxy-β-d-glucopyranose, a disaccharide having an unusual α-d-(1→3) linkage

✍ Scribed by Marianna Strumpel; Heinz-Jürgen Schmidt; Peter Luger; Hans Paulsen

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
1005 KB
Volume
125
Category
Article
ISSN
0008-6215

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✦ Synopsis

The crystal structure of 3-0-(6-0-acetyl-2,4-diazido-3-O-benzyl-2,4-dideoxy-~~-D-glucopyranosyl)-1,6-anhydro-2,4-diazido-2,4-dideoxy-P-D-glUCOpyranOSe, C21H24N1207, mol. wt. 556.5, was investigated by X-ray analysis. The disaccharide crystallizes in the triclinic space group Pl, with a = 889.3(5), b = 869.6(5), and c = 999.5(6) pm, and cy = 105.83(4)", p = 116.22(4)", y = 88.42(4)", Z = 1, and p = 1.394 g.cm -3. Phase determination failed with direct methods, but, as the 1,6anhydride component of the molecule was already known from a previous structure analysis, the vector-search method could be applied in solving the structure. Diffractometer data were refined to an R value of 0.063 (R, = 0.080) for 2102 observed reflections. The anhydro-bridged system has a distorted l&(D) conformation, in agreement with that of other anhydropyranoses so far investigated. A comparison shows that, for the specific kind of distortion, mainly the anti-reflex effect is reponsible, whereas 1,3-diaxial interactions have a minor influence. The nonbridged ring adopts an almost perfect "C,(D) conformation. The anomeric effect is observed in both of the sugar-ring systems in terms of bond-length shortening. The disaccharide has an a-D-Glc-4C,-(la+3e)-D-Glc-'C4 glycosidic linkage. No previous X-ray investigation of a compound of this type is known. The pyranoid rings are almost perpendicular to each other. The @, $ angles of the glycosidic linkage are +78.1(5) and -86.0(4)". The magnitude of the 6, value is in agreement with the predictions of the exo-anomeric effect. The glycosidic @and Cc, angles were very well reproduced by empirical calculations using the HSEA approach.

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