3,4-Dicyanophenyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyranoside
نویسندگان
چکیده
The title compound, C(22)H(22)N(2)O(10), was prepared by the glycosidation method through nitrite displacement on substituted nitro-phthalonitrile. The mol-ecule contains a benzene ring, two nitrile groups and an acetyl-protected d-glucose fragment which adopts a chair conformation. The absolute configuration was determined by the use of d-glucose as starting material. All substituents of the protected sugar are in equatorial positions, with the exclusive presence of the α-anomer. The crystal packing is stabilized by C-H⋯O and C-H⋯N hydrogen-bonding inter-actions.
منابع مشابه
Isopropyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside
The title compound, C(17)H(26)O(10), was formed by a Koenigs-Knorr reaction of 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide and propan-2-ol. The central ring adopts a chair conformation. The crystal does not contain any significant inter-molecular inter-actions.
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THE TITLE COMPOUND [SYSTEMATIC NAME: (2R,3R,4S,5R,6R)-2-(acet-oxy-meth-yl)-6-propoxytetra-hydro-2H-pyran-3,4,5-triyl triacetate], C(17)H(26)O(10), was formed by a Koenigs-Knorr reaction of 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide and n-propanol. The central ring adopts a chair conformation. The crystal does not contain any significant inter-actions such as hydrogen bonds.
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In the crystal structure of the title compound, C(24)H(27)NO(11), a substituted tetra-acetyl glucopyran-oside derivative, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into ribbons propagated in [010]. The d configuration has been attributed on the basis of the synthesis and the β anomer has been determined from the structure.
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Starting from allyl 2-O-acetyl-3-O-benzyl-α-l-rhamnopyranoside (3), allyl (2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl)-(1→4)-2-O-acetyl-3-O-benzyl-α-l-rhamnopyranoside (5) was synthesized under Helferich conditions. Module 5 was converted to 2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl-(1→4)-2-O-acetyl-3-O-benzyl-α-l-rhamnopyranosyl bromide (8) which was then coupled with methyl (allyl 2,3-di...
متن کامل4-(Dimethoxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside
The enanti-omerically pure title compound, C(23)H(30)O(12), crystallizes in the chiral space group P2(1)2(1)2(1). The O-acetyl-ated-glucopyran-oside moiety adopts a chair conformation. Numerous C-H⋯O inter-actions as well as a C-H⋯π inter-action are present in the crystal structure.
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