4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fuco-pyranos-yl)-1H-1,2,3-triazole.
4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fuco-pyranos-yl)-1H-1,2,3-triazole.
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4-丁基-1-(2,3,4-三-O-乙酰基-β-l-岩藻糖-吡喃基)-1H-1,2,3-三唑。
DOI：
10.1107/s1600536809028700
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
Zeller,Matthias
中科院分区：
文献类型：
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作者：
Alhassan,Abdul-Basit;Norris,Peter;Zeller,Matthias
作为 N-糖基-1,2,3-三唑合成研究的一部分，标题化合物 C18H27N3O7 通过 CuI 催化叠氮化物与炔烃的偶联合成。晶体结构证实了吡喃糖N-糖苷的β-构象异构体的选择性形成，从而证实了在N-糖基三唑基团占据异头C原子的赤道位置的杂环形成过程中立体化学的保留。该结构呈现出两个晶体学上独立的分子（A 和 B），具有基本相同的构象，加权均方根为偏差仅为 0.09 Å。这些分子按层排列，一方面具有由丁基三唑单元构成的疏水性和极性较大的部分，另一方面具有由碳水化合物单元主导的极性较大的部分。在极性层内，分子间相互作用由弱 C—H⋯O 氢键的三维网络主导，乙酰酮 O 原子作为氢键受体。三唑单元通过 C—H⋯N 氢键相互作用，将分子连接成两条无限的分子链，由 A 分子或 B 分子组成，沿着 [100] 彼此平行延伸。丁基之间没有观察到定向相互作用。
The title compound, C18H27N3O7, was synthesized by CuI-catalysed coupling of an azide with an alkyne as part of a study into the synthesis of N-glycosyl-1,2,3-triazoles. The crystal structure confirms the selective formation of the β-conformer of the pyranose N-glycoside, thus confirming the retention of stereochemistry during heterocycle formation with the N-glycosyl triazole group occupying the equatorial position at the anomeric C atom. The structure exhibits two crystallographically independent molecules (A and B) with essentially identical conformations with a weighted r.m.s. deviation of only 0.09 Å. The molecules are arranged in layers with hydrophobic and more polar sections built from the butyl triazole units on the one hand and the more polar moieties dominated by the carbohydrate units on the other. Within the polar layers, intermolecular interactions are dominated by a three-dimensional network of weak C—H⋯O hydrogen bonds with the acetyl keto O atoms as the hydrogen-bond acceptors. The triazole units interact with each other via C—H⋯N hydrogen bonds which connect the molecules into two infinite chains of molecules made up of either A molecules or B molecules that stretch parallel to each other along [100]. Between the butyl groups no directional interactions are observed.