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1,3,4-三-O-乙酰基-2-N-(三氟乙酰基)-β-L-岩藻糖

1,3,4-Tri-O-acetyl-2-N-(tri-fluoro-acetyl)-β-l-fucose.

作者信息

McCutcheon David C, Norris Peter, Zeller Matthias

机构信息

Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, OH 44555-3663, USA.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2014 Jan 15;70(Pt 2):o134-5. doi: 10.1107/S1600536813034958. eCollection 2014 Feb 1.

Abstract

The title compound, C14H18F3NO8, was produced through conjugation of 1,3,4-tri-O-acetyl-2-azidode-oxy-α,β-l-fucose with tri-fluoro-acetyl chloride in the presence of bis-(di-phenyl-phosphino)ethane in tetra-hydro-furan at room temperature. The X-ray crystal structure reveals that the β-anomer of the product mixture crystallizes from ethyl acetate/hexa-nes. The compound exists in a typical chair conformation with the maximum possible number of substituents, four out of five, located in the sterically preferred equatorial positions. The major directional force facilitating packing of the mol-ecules are N-H⋯O hydrogen bonds involving the amide moieties of neighboring mol-ecules, which connect mol-ecules stacked along the a-axis direction into infinite strands with a C (1) 1(4) graph-set motif. Formation of the strands is assisted by a number of weaker C-H⋯O inter-actions involving the methine and methyl H atoms. These strands are connected through further C-H⋯O and C-H⋯F inter-actions into a three dimensional network.

摘要

标题化合物C₁₄H₁₈F₃NO₈是在室温下,于四氢呋喃中,在双(二苯基膦基)乙烷存在的情况下,通过1,3,4 - 三 - O - 乙酰基 - 2 - 叠氮基 - 脱氧 - α,β - l - 岩藻糖与三氟乙酰氯共轭反应制得。X射线晶体结构表明,产物混合物的β - 异头物从乙酸乙酯/己烷中结晶出来。该化合物以典型的椅式构象存在,五个取代基中的四个处于空间位阻较小的赤道位置,达到最大可能数量。促进分子堆积的主要定向力是涉及相邻分子酰胺部分的N - H⋯O氢键,其将沿a轴方向堆叠的分子连接成具有C(1)1(4)图集模式的无限链。链的形成还受到一些涉及次甲基和甲基H原子的较弱C - H⋯O相互作用的辅助。这些链通过进一步的C - H⋯O和C - H⋯F相互作用连接成三维网络。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/56a8/3998300/f30e50437383/e-70-0o134-fig1.jpg

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