2-喹喔啉甲醛,腙 | 192717-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-喹喔啉甲醛,腙
• 英文名称: (4-nitro)phenyl β-D-glucofuranoside
• 英文别名: 4-nitrophenyl β-D-glucofuranoside；p-nitrophenyl β-D-glucofuranoside；(2R,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-(4-nitrophenoxy)oxolane-3,4-diol
• CAS: 192717-86-5
• 化学式: C₁₂H₁₅NO₈
• 分子量: 301.253
• InChiKey: RMQNVZDXEMOJCW-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 在 硫酸 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 2-喹喔啉甲醛,腙
  参考文献：
  名称：

  Non-natural aldofuranosides as substrates of a β-glucosidase

  摘要：

  Based on glycosidase inhibitory activities of some known 1,4-iminoalditols, four aldofuranosides, (4-nitro)phenyl beta-D-glucofuranoside, -beta-D-galactofuranoside, -alpha-L-idofuranoside and -alpha-L-altrofuranoside, were identified as possible substrates of glucosidases and galactosidases. Three of them were found to be accepted by the beta-glucosidase from Agrobacterium sp. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.027

文献信息

• Glucofuranosylation with penta-O-propanoyl-β-d-glucofuranose
  作者：Richard H. Furneaux、Bénédicte Martin、Phillip M. Rendle、Carol M. Taylor

  DOI：10.1016/s0008-6215(02)00300-2

  日期：2002.11

  be a suitable glycosylating agent for the acid-catalysed, direct synthesis of O-, S- and N-glucofuranosyl compounds. Beta-linked products are formed with good selectivity. Reaction with cyanotrimethylsilane gave the 1,2-O-(1-cyanopropylidene)acetal rather than the C-glycosyl cyanide. By selective acid-catalysed hydrolysis, the title compound was converted to the 1-hydroxy analogue from which the trichloroacetimidates

  容易获得的结晶五-O-丙酰基-β-D-葡萄糖呋喃糖被证明是用于酸催化的O-，S-和N-葡萄糖呋喃糖基化合物的直接合成的合适的糖基化剂。β-连接的产物具有良好的选择性。与氰基三甲基硅烷反应得到1,2-O-（1-氰基亚丙基）缩醛而不是C-糖基氰化物。通过选择性的酸催化水解，将标题化合物转化为1-羟基类似物，由此可制得三氯乙亚氨酸酯作为其他潜在的糖基化剂。
• An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase
  作者：Caroline Rémond、Richard Plantier-Royon、Nathalie Aubry、Michael J. O’Donohue

  DOI：10.1016/j.carres.2005.01.016

  日期：2005.3

  Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. Importantly, galactofuranose is a key constituent of major cell envelope polysaccharides in pathogenic mycobacteria. In this respect, galactofaranose-based glycoconjugates are interesting target molecules for drug design. O-Glycosidases and notably beta-D-galactofuranosidases could be useful tools for the chemoenzymatic synthesis of galacto furano sides, but to date no studies of this type have been reported. Here we report the use of a GH 51 alpha-L-arabinofuranosidase for the synthesis Of beta-D-galactofuranosides. We have demonstrated that this enzyme can catalyse both the autocondensation of p-nitrophenyl-beta-D-galactofuranoside and the transgalactofuranosylation of benzyl alpha-D-xylopyranoside, forming p-nitrophenyl beta-D-galactofuranosyl-(1 -> 2)beta-D-galactofuranoside and benzyl beta-D-galactofuranosyl-(1 -> 2)-alpha-D-xylopyranoside, respectively. Both reactions were very regiospecific and the reaction involving benzyl alpha-D-xylopyranoside afforded very high yields (74.8%) of the major product. To our knowledge, this demonstration of chemoenzymatic synthesis of galactofuranosides constitutes the very first use of an O-glycosidase for the synthesis of galactofuranosides. (c) 2005 Elsevier Ltd. All rights reserved.
• US6620921B1
  申请人：——

  公开号：US6620921B1

  公开（公告）日：2003-09-16
• [EN] GLUCOFURANOSES<br/>[FR] GLUCOFURANOSES
  申请人：IND RES LTD

  公开号：WO2001036435A1

  公开（公告）日：2001-05-25

  A β-D-glucofuranose compound which is 1,2,3,5,6-penta-O-propanoyl-β-D-glucofuranose, preferably in crystalline form, is prepared from D-glucose. The compound is prepared by reacting D-glucose with boric acid, or an equivalent thereof, followed by treatment with a propanoylating reagent, preferably propanoic anhydride. The compound is useful for the preparation of other compounds, such as glucofuranosides.
• Non-natural aldofuranosides as substrates of a β-glucosidase
  作者：Andreas Tauss、Peter Greimel、Karen Rupitz、Andreas J. Steiner、Arnold E. Stütz、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.tetasy.2004.11.027

  日期：2005.1

  Based on glycosidase inhibitory activities of some known 1,4-iminoalditols, four aldofuranosides, (4-nitro)phenyl beta-D-glucofuranoside, -beta-D-galactofuranoside, -alpha-L-idofuranoside and -alpha-L-altrofuranoside, were identified as possible substrates of glucosidases and galactosidases. Three of them were found to be accepted by the beta-glucosidase from Agrobacterium sp. (C) 2004 Elsevier Ltd. All rights reserved.