1-O-(p-nitrophenyl)-4,6-O-benzylidene-β-D-glucopyranoside | 118396-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(p-nitrophenyl)-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: 4-nitrophenyl 4,6-O-benzylidene-β-D-glucopyranoside；p-nitrophenyl 4,6-O-benzylidene-β-D-glucopyranoside；(4-nitro-phenyl)-[O⁴,O⁶-((R)-benzylidene)-β-D-glucopyranoside]；(4-Nitro-phenyl)-[O⁴,O⁶-((R)-benzyliden)-β-D-glucopyranosid]；(2R,4aR,6S,7R,8R,8aS)-6-(4-nitrophenoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 118396-60-4
• 化学式: C₁₉H₁₉NO₈
• 分子量: 389.362
• InChiKey: BGBDVEKOBCWPHZ-MGYGNFHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-(p-nitrophenyl)-4,6-O-benzylidene-β-D-glucopyranoside 在 三乙烯二胺 、 咪唑 、 N-甲基吲哚酮 、 K₂OsO₂(H₂O)2 、 碘 、 三苯基膦 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 反应 17.0h， 生成 4-nitrophenyl 4,6-O-benzylidene-β-D-allopyranoside
  参考文献：
  名称：

  Stereospecific synthesis of β-d-allopyranosides by dihydroxylation of β-d-erythro-2,3-dideoxyhex-2-enopyranosides

  摘要：

  The synthesis of 4,6-O-benzylidene-beta -D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give beta -D-allopyranosides in moderate to excellent yield. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00181-1
• 作为产物：
  描述：

  4-硝基苯-Β-D-吡喃葡萄糖苷 在 苯甲醛 、 zinc(II) chloride 作用下， 生成 1-O-(p-nitrophenyl)-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Jermyn, Australian Journal of Chemistry, 1957, vol. 10, p. 448,450

  摘要：

  DOI：

文献信息

• Synthesis of p-trifluoroacetamidophenyl β-d-glucopyranoside 4-(d-ribit-5-yl phosphate) corresponding to the Haemophilus influenzae type a capsular antigen
  作者：Björn Classon、Per J. Garegg、Ingvar Lindh

  DOI：10.1016/0008-6215(88)84107-7

  日期：1988.8

  The synthesis is described of the title glycoside which corresponds to the Haemophilus influenzae type a capsular antigen. The hydrogenphosphonate method was used with 3,3'-(chlorophosphonylidene)bis(2-oxo-1,3-oxazolidene) as the condensing agent.

  描述了标题糖苷的合成，其对应于流感嗜血杆菌型荚膜抗原。氢膦酸盐法以3，3′-（氯膦基亚甲基）双（2-氧代-1，3-恶唑基）为缩合剂。
• New sugar-based gelators with an amino group, the gelation ability of which is remarkably reinforced by the hydrogen bond and the metal coordination
  作者：Natsuki Amanokura、Yasumasa Kanekiyo、Seiji Shinkai、David N. Reinhoudt

  DOI：10.1039/a903298c

  日期：——

  Three sugar-integrated gelators bearing a p-aminophenyl group which are expected to exert a hydrogen-bonding effect and a metal coordination effect on the gelation ability were synthesised. α-D-Galactose-based 2b was only soluble or precipitated and β-D-glucose-based 4b gelated only two of 15 solvents tested herein whereas α-D-glucose-based 1b acted as an excellent gelator which could gelate 8 solvents. The sol–gel phase-transition temperature (Tgel) values for 1b were higher by 41–78 °C than those for α-D-glucose-based 1a bearing a p-nitrophenyl group. The spectral studies indicated that this gel reinforcement is due to the hydrogen-bonding interaction including the amino group. The Tgel values for the ethanol gel of 1b were markedly improved by the addition of AgNO3, CoCl2 or CdCl2. The detailed examination of a 1b + CoCl2 gel system in ethanol showed that the gel is stabilised by the ‘cross-link’ of 1b molecules by the Co(II)–amino group interaction. This is the first and a convenient method for the metal reinforcement of organic gels.

  α-D-半乳糖基 2b 只能溶解或沉淀，β-D-葡萄糖基 4b 在 15 种测试溶剂中只能凝胶两种溶剂，而α-D-葡萄糖基 1b 则是一种出色的凝胶剂，可以凝胶 8 种溶剂。1b 的溶胶-凝胶相变温度（Tgel）值比带有对硝基苯基的 α-D 葡萄糖基 1a 高 41-78 ℃。光谱研究表明，这种凝胶强化是由于包括氨基在内的氢键相互作用造成的。加入 AgNO3、CoCl2 或 CdCl2 后，1b 的乙醇凝胶的 Tgel 值明显提高。对乙醇中 1b + CoCl2 凝胶体系的详细研究表明，凝胶是通过 Co（II）-氨基相互作用使 1b 分子 "交联 "而稳定的。这是第一种对有机凝胶进行金属强化的便捷方法。
• Stereospecific synthesis of β-d-allopyranosides by dihydroxylation of β-d-erythro-2,3-dideoxyhex-2-enopyranosides
  作者：Paul V Murphy、Julie L O'Brien、Amos B Smith

  DOI：10.1016/s0008-6215(01)00181-1

  日期：2001.9

  The synthesis of 4,6-O-benzylidene-beta -D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give beta -D-allopyranosides in moderate to excellent yield. (C) 2001 Published by Elsevier Science Ltd.
• Jermyn, Australian Journal of Chemistry, 1957, vol. 10, p. 448,450
  作者：Jermyn

  DOI：——

  日期：——