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7-叠氮基-N,N-二乙基-4,5-O-异丙叉基-4-C-甲基-3,6-脱水-7-脱氧-D-甘油-D-甘露庚酰胺

7-Azido-N,N-diethyl-4,5-O-isopropyl-idene-4-C-methyl-3,6-anhydro-7-de-oxy-d-glycero-d-manno-heptonamide.

作者信息

Jenkinson Sarah F, Wang Chen, Pino-González Maria-Soledad, Fleet George W J, Watkin David J

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2009 Jan 8;65(Pt 2):o263. doi: 10.1107/S1600536808044279.

Abstract

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.

摘要

5-叠氮基-5-脱氧-2,3-O-异丙叉基-2-C-甲基-D-核糖与N,N-二乙基-2-(二甲基硫亚基)乙酰胺反应生成了标题化合物C(15)H(26)N(4)O(5),这是主要产物,最初形成的环氧化物随后被游离的4-羟基的分子内攻击打开。X射线晶体学确定了标题化合物的相对立体化学,并且通过使用D-核糖作为起始原料确定了绝对构型。晶体结构包含平行于a轴排列的分子链,通过弱的分叉O-H⋯(N,N)氢键相连。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce0e/2968166/6aeb33120a7f/e-65-0o263-fig1.jpg

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