Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 12 (December 2012)


organic compounds



cu3015 scheme

Acta Cryst. (2012). C68, o502-o506    [ doi:10.1107/S0108270112046689 ]

Methyl 4-O-[beta]-D-mannopyranosyl [beta]-D-xylopyran­oside

W. Zhang, A. G. Oliver, H. M. Vu, J. G. Duman and A. S. Serianni

Abstract: Methyl [beta]-D-mannopyranosyl-(1[rightwards arrow]4)-[beta]-D-xylopyran­oside, C12H22O10, (I), crystallizes as colorless needles from water, with two crystallographically independent mol­ecules, (IA) and (IB), comprising the asymmetric unit. The inter­nal glycosidic linkage conformation in mol­ecule (IA) is characterized by a [varphi]' torsion angle (O5'Man-C1'Man-O1'Man-C4X­yl; Man is mannose and Xyl is xylose) of -88.38 (17)° and a [psi]' torsion angle (C1'Man-O1'Man-C4Xyl-C5Xyl) of -149.22 (15)°, whereas the corresponding torsion angles in mol­ecule (IB) are -89.82 (17) and -159.98 (14)°, respectively. Ring atom numbering conforms to the convention in which C1 denotes the anomeric C atom, and C5 and C6 denote the hy­droxy­methyl (-CH2OH) C atom in the [beta]-Xylp and [beta]-Manp residues, respectively. By comparison, the inter­nal glycosidic linkage in the major disorder component of the structurally related disaccharide, methyl [beta]-D-galactopyranosyl-(1[rightwards arrow]4)-[beta]-D-xylo­pyran­oside), (II) [Zhang, Oliver & Serriani (2012). Acta Cryst. C68, o7-o11], is characterized by [varphi]' = -85.7 (6)° and [psi]' = -141.6 (8)°. Inter-residue hydrogen bonding is observed between atoms O3Xyl and O5'Man in both (IA) and (IB) [O3Xyl...O5'Man inter­nuclear distances = 2.7268 (16) and 2.6920 (17) Å, respectively], analogous to the inter-residue hydrogen bond detected between atoms O3Xyl and O5'Gal in (II). Exocyclic hy­droxy­methyl group conformation in the [beta]-Manp residue of (IA) is gauche-gauche, whereas that in the [beta]-Manp residue of (IB) is gauche-trans.

Formula: C12H22O10


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