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Molecular and crystal structures of 2,3,4,6,1′,3′,4′,6′-octa-O-acetyl-β-sophorose, methyl 2,3,4,6,3′,4′,6′-hepta-O-acetyl-β-sophoroside, and methyl 2,3,4,6,3′,4′-hexa-O-acetyl-6′-deoxy-β-sophoroside

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
271
Issue
2
Identifiers
DOI: 10.1016/0008-6215(95)00093-9
Keywords
  • β-Sophorose Octaacetate
  • Methyl β-Sophoroside Heptaacetate
  • Methyl 6′-Deoxy-β-Sophoroside Hexaacetate

Abstract

Abstract The molecular and crystal structures of 2,3,4,6,1′,3′,4′,6′-octa- O-acetyl-β-sophorose (β-sophorose octaacetate), methyl 2,3,4,6,3′,4′,6′-hepta- O-acetyl-β-sophoroside (methyl β-sophoroside heptaacetate), and methyl 2,3,4,6,3′,4′-hexa- O-acetyl-6′-deoxy-β-sophoroside (methyl 6′-deoxy-β-sophoroside heptaacetate) were determined by X-ray diffraction. All structures were obtained by the direct method and refined by the full-matrix least-squares procedure. The crystal data and final R values are as follows: (β-sophorose octaacetate, C 28O 19H 38, monoclinic, P2 1, a = 15.529(4), b = 10.958(2), c = 10.804(2) A ̊ , β = 107.73(3)°, D obsd = 1.285 g cm −3, D calcd = 1.288 g cm −3, Z = 2, R = 0.052, R W = 0.052 ; methyl β-sophoroside heptaacetate, C 27O 18H 38, orthorhombic, P2 12 12 1, a = 20.992(5), b = 27.642(7), c = 5.730(2) A ̊ , D obsd = 1.305 g cm −3, D calcd = 1.295 g cm −3, Z = 4, R = 0.064, R W = 0.066 ; methyl 6′-deoxy-β-sophoroside hexaacetate, C 25O 16H 36, hexagonal, P6 5, a = b = 15.136(2), c = 23.534(4) A ̊ , D calcd = 1.264 g cm −3, Z = 6, R = 0.079, R W = 0.064 . All the d-glucose residues have the 4 C 1 pyranose conformation. These three molecules interact with their surrounding molecules by van der Waals forces, only. Conformational angles of φ and ω at the β (1 → 2) glycosidic linkage of these compounds are similar to each other and close to the energetically minimum positions. All the primary acetate substituents at C-6 take a gauche-gauche conformation.

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