Methyl 3,4-O-dibenzoyl-2-O-benzyl-1-thio-β-l-fucopyranoside
✍ Scribed by Bornaghi, Laurent F. ;Drinnan, Nicholas B. ;Ramsdale, Tracie ;Healy, Peter C. ;White, Alan R.
- Publisher
- International Union of Crystallography
- Year
- 2005
- Tongue
- English
- Weight
- 223 KB
- Volume
- 61
- Category
- Article
- ISSN
- 1600-5368
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📜 SIMILAR VOLUMES
The molecule of the title compound, C 29 H 35 ClO 15 S, possesses normal geometric parameters. Intermolecular C-HÁ Á ÁO hydrogen-bond interactions are responsible for the supramolecular assembly of the complex molecules into a threedimensional framework.
The major product of the acetylation of l-fucose using acetic anhydride (Ac 2 O) in pyridine was identifed by single-crystal diffraction at 100 K as 1,2,3,4-tetra-O-acetyl--l-fucopyranose, C 14 H 20 O 9 .
Single-crystal X-ray study T = 100 K Mean '(C±C) = 0.003 A Ê R factor = 0.039 wR factor = 0.094 Data-to-parameter ratio = 8.3 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
In the title compound, C 27 H 38 O 4 SSi, the furanose ring adopts a nearly perfect E 4 envelope conformation, while the sixmembered ring containing the Si atom exists in an approximate half-chair conformation. The conformation about the glycosidic linkage is that favored by the exo-anomeric effect.
Condensation of 2,4-di-O-acetyl-3,6-di-O-methyl-a-~glucopyranosyl bromide with either ally1 or benxyl2,4-di-0-methyl-cu+rhamnopyranoside in the presence of mercuric cyanide, followed by 0-deacetylation, gave the title oligosaccharides in excellent yields.