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Synthesis, crystal structure, and conformation of 3-O-(6-O-acetyl-2,3-anhydro-4-deoxy-α-l-ribo-hexopyranosyl)-1,2:5,6-di-O-isopropylidene-α-d-glucofuranose

✍ Scribed by Janusz W. Krajewski; Przemysław Gluziński; Zofia Urbańczyk-Lipkowska; Anna Banaszek; Max Dobler

Publisher: Elsevier Science
Year: 1984
Tongue: English
Weight: 638 KB
Volume: 134
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(84)85018-1

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✦ Synopsis

3-0-(6-0-Acetyl-2,3-anhydro-4-deoxy-a-L-ribo-hexopyranosyl)-l,2:5,6-di-O-isopropylidene-a-D-glucofuranose has been synthesised and its monocrystal investigated by X-ray diffraction methods. The compound crystallises in the orthorhombic system, space group P2,2,2t, with cell constants a = 8.790( 7), b = 11.678(4), and c = 21.457(10) A. The intensity data were collected with a fourcircle CAD-4 diffractometer. From a total of 1684 intensities, 1275 were of I > 20,. The structure was solved by direct methods and refined by the full-matrix, leastsquares procedure, resulting in R 0.057. The 4-deoxy-2,3_anhydropyranose ring is characterised by a sofa conformation (&), the 1,2-0-isopropylidene ring has a hybrid conformation (E + T), and the 5,6-0-isopropylidene and the (Y-Dglucofuranose rings have twist (T) conformations.

The 4 and + torsion angles for the glycosidic linkage are 54(4)" and 29(4)", respectively.

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