7-Azido-N,N-diethyl-4,5-O-isopropylidene-4-C-methyl-3,6-anhydro-7-deoxy-d-glycero-d-manno-heptonamide
نویسندگان
چکیده
The reaction of 5-azido-5-de-oxy-2,3-O-isopropyl-idene-2-C-methyl-d-ribose with N,N-diethyl-2-(dimethyl-sulfuranyl-idene)acetamide gave the title compound, C(15)H(26)N(4)O(5), as the major product arising from initial formation of an epoxide which was subsequently opened by intra-molecular attack of the free 4-hydroxyl group. X-ray crystallography confirmed the relative stereochemistry of the title compound and the absolute configuration was determined by the use of d-ribose as the starting material. The crystal structure contains chains of mol-ecules running parallel to the a axis, being linked by weak bifurcated O-H⋯(N,N) hydrogen bonds.
منابع مشابه
6-Azido-3-O-benzyl-6-deoxy-N,N-diethyl-1,2-O-isopropylidene-d-glycero-α-d-gluco-heptofuranuronamide
Reaction of 3-O-benzyl-1,2-O-isopropyl-idene-α-xylo-pentodialdo-1,4-furan-ose with N,N-diethyl-2-(dimethyl-sulfuranil-idene)acetamide gave stereoselectively an ep-oxy-amide, which was regioselectively opened by NaN(3) in dimethyl formamide to give the title compound, C(21)H(30)N(4)O(6). X-ray crystallography confirmed the relative stereochemistry of the title compound and the absolute configura...
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The relative stereochemistry of the title compound, C(10)H(15)N(3)O(5), was confirmed by the crystal structure determin-ation. The absolute configuration was determined from the use of d-lyxonolactone as the starting material. The six-membered ring adopts a boat conformation with the larger azide group, rather than the methyl group, in the bowsprit position. In the crystal structure, a bifurcat...
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