3-Ethyl-8-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyloxy)quinolin-2(1H)-one
نویسندگان
چکیده
The structure of the title compound, C(26)H(31)NO(12), contains an essentially planar quinoline skeleton, with the maximum deviation from the best plane being 0.055 (2) Å, and an oxane ring in a classical chair conformation with the following Cremer and Pople puckering parameters: Q = 0.586 (2) Å, θ = 11.5 (2)° and ϕ = 309.4 (10)°. One acetyl group displays rotational disorder with occupancies of 0.634 (8):0.366 (8). The crystal packing is stabilized by N-H⋯O hydrogen bonds, which link mol-ecules into chains along the a axis. The packing is further stabilized by weak C-H⋯O interactions. The absolute configurations on the carbons in the oxane ring correspond to those of the commercial starting material and are unchanged in the well known mechanism of the Koenigs-Knorr synthesis.
منابع مشابه
Efficient synthesis of building blocks for branched rhamnogalacturonan I fragments.
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 کاملSynthesis and NMR studies of malonyl-linked glycoconjugates of N-(2-aminoethyl)glycine. Building blocks for the construction of combinatorial glycopeptide libraries
Four glycoconjugate building blocks for the construction of combinatorial PNA like glycopeptide libraries were prepared in 75-79% yield by condensing tert-butyl N-[2-(N-9-fluorenylmethoxycarbonylamino)ethyl]glycinate (AEG) 5 with 3-oxo-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamino)- (6a), 3-oxo-3-(β-D-galactopyranosylamino)- (6b), 3-oxo-3-(2-acetamido-2-deoxy-3,4,6-tetra-O-acetyl-β-D-glucop...
متن کامل(2R,3S)-2-Benzyl-3-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyloxy)butanolide
The title compound, C(25)H(30)O(12), which demonstrates a significant hepatoprotective effect, has comparable geometrical parameters to those of similar compounds. The absolute configuration of the title compound, viz. 2R,3S, was identified from the Flack parameter of 0.05 (17) and the Hooft parameter of 0.04 (6).
متن کامل2,3,4,6-Tetra-O-acetyl-β-d-galactopyranosyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl disulfide tetrahydrofuran solvate
The asymmetric unit of title compound, C(28)H(38)O(18)S(2)·C(4)H(8)O, comprises one disulfide-bridged sugar molecule and one solvent molecule. No significant differences in structural parameters are found between the present structure and the previously determined unsolvated form [Brito, López-Rodríguez, Bényei & Szilagyi (2006 ▶). Carbohydr. Res.341, 2967-2972]. The compounds are characterized...
متن کامل5'-Uridyl derivatives of N-glycosyl allophanic acid and biuret.
(2',3'-O-Isopropylidene-5'-uridyl) 4-(2,3,4,6-tetra-O-acetyl-beta-d-glycopyranosyl)allophanates were obtained in the reactions of 2',3'-O-isopropylidene-uridine and O-peracetylated beta-d-gluco-, galacto- and xylopyranosylamines, and OCNCOCl. 2,3,4,6-Tetra-O-acetyl-beta-d-glucopyranosyl isocyanate and N-(2',3'-O-isopropylidene-5'-uridyl)urea gave 1-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 66 شماره
صفحات -
تاریخ انتشار 2010