1-O-(o-nitrobenzyl)-4,6-O-benzyliden-β-D-glucopyranoside | 341035-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-O-(o-nitrobenzyl)-4,6-O-benzyliden-β-D-glucopyranoside
• 英文别名: (4aR,6R,7R,8R,8aS)-6-[(2-nitrophenyl)methoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 341035-13-0
• 化学式: C₂₀H₂₁NO₈
• 分子量: 403.389
• InChiKey: OVKCETQEPKDTRO-YMUIMLINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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-(o-nitrobenzyl)-4,6-O-benzyliden-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 碘 、 4-(dimethylamino)pyridine hydrochloride 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-nitrobenzyl 2,3-bis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside
  参考文献：
  名称：

  鞣花单宁化学。Tellimagrandin II和Corariariin A的含脱氢二氢二甲酰基醚的二聚半乳甘油类似物的合成。

  摘要：

  天然存在的鞣花单宁tellimagrandin II的首次化学合成已有报道。合成的关键步骤包括在吡喃葡萄糖核心的O（4）和O（6）位置适当保护的没食子酰基环的atropselective氧化偶联，和衍生的异头醇与没食子酰氯的立体选择性酰化。另外，描述了新的没食子鞣质-鞣花单宁杂交体的合成。该二聚体构建体依赖于杂Diels-Alder环加成/还原性重排序列，以从基于单体五烷基酰葡萄糖的邻醌递送完整骨架。

  DOI：

  10.1021/jo9816966
• 作为产物：
  描述：

  苯甲醛 、 1-O-(o-nitrobenzyl)-β-D-glucopyranose 在 zinc(II) chloride 作用下， 反应 16.0h， 以90%的产率得到1-O-(o-nitrobenzyl)-4,6-O-benzyliden-β-D-glucopyranoside
  参考文献：
  名称：

  Ellagitannin Chemistry. The First Total Chemical Synthesis of an O(2),O(3)-Galloyl-Coupled Ellagitannin, Sanguiin H-5

  摘要：

  The biomimetic synthesis of sanguiin H-5 (1) was accomplished through the diastereoselective formation of the crucial biphenyl carbon-carbon bond between galloyl moieties at the O(2) and O(3) positions of an appropriately protected glucose-derived precursor. Furthermore, the beta-anomeric galloyl linkage was established with complete stereochemical control.

  DOI：

  10.1021/jo00130a016

文献信息

• [EN] GALLOTANNINS AND ELLAGITANNINS AS REGULATORS OF CYTOKINE RELEASE<br/>[FR] GALLOTANIN ET ELLAGITANIN EN TANT QUE REGULATEURS DE LA LIBERATION DE CYTOKINES
  申请人：PENN STATE RES FOUND

  公开号：WO2001036436A1

  公开（公告）日：2001-05-25

  A means and method for increasing or inhibiting the secretion of cytokines using gallotannins and ellagitannins is described. The preferred cytokine release inhibiting compounds are dimeric gallotannins having a linker molecule that misaligns the carbohydrate cores of the compounds. The preferred cytokine release promoting gallotannins and ellagitannins include a diaryl ether linker unit. In comparison to the more structurally complex ellagitannins, the compounds of this invention are structurally simpler, easier to synthesize, and more potent.

  本发明涉及使用没食子酸和榄香酸类物质增加或抑制细胞因子的分泌的方法和手段。首选的抑制细胞因子释放的化合物是二聚没食子酸，其具有使化合物的碳水化合物核心错位的连接分子。首选的促进细胞因子释放的没食子酸和榄香酸类包括一个二芳基醚连接单元。与结构更复杂的榄香酸类相比，本发明的化合物结构更简单，易于合成且更有效。
• GALLOTANNINS AND ELLIGITANNINS AS REGULATORS OF CYTOKINE RELEASE
  申请人：FELDMAN KENNETH S.

  公开号：US20080070850A1

  公开（公告）日：2008-03-20

  A means and method for increasing or inhibiting the secretion of cytokines using gallotannins and ellagitannins is described. The preferred cytokine release inhibiting compounds are dimeric gallotannins having a linker molecule that misaligns the carbohydrate cores of the compounds. The preferred cytokine release promoting gallotannins and ellagitannins include a diaryl ether linker unit. In comparison to the more structurally complex ellagitannins, the compounds of this invention are structurally simpler, easier to synthesize, and more potent.

  本发明描述了使用没食子酸单宁和榄皮酸单宁增加或抑制细胞因子分泌的方法和手段。优选的细胞因子释放抑制化合物是具有链接分子的二聚没食子酸单宁，该链接分子使化合物的碳水化合物核心错位。优选的细胞因子释放促进没食子酸单宁和榄皮酸单宁包括一个二芳基醚链接单元。与结构更为复杂的榄皮酸单宁相比，本发明的化合物结构更简单，更易于合成，且更具有活性。
• Synthesis of Enantiomerically Pure Unusual Ellagitannins 1,4,6-Tri-<i>O</i>-galloyl-2,3-(<i>R</i>)-hexahydroxydiphenoyl-β-<scp>d</scp>-glucopyranoside and 4,6-Di-<i>O</i>-galloyl-2,3-(<i>R</i>)-hexahydroxydiphenoyl-<scp>d</scp>-glucoside. The Proposed Chemical Structures for Cercidinin A and B Must Be Revised
  作者：Karamali Khanbabaee、Kerstin Lötzerich

  DOI：10.1021/jo9805302

  日期：1998.11.1

  The total syntheses of the enantiomerically pure unusual ellagitannins 1,4,6-tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-beta-D-glucopyranoside (1) and 4, 6-di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-D-glucoside (2) are reported. The NMR data of the synthetic ellagitannins 1 and 2 are not identical with those reported for cercidinin A and B. Thus, the proposed structures for cercidinin A and B must be revised.
• GALLOTANNINS AND ELLAGITANNINS AS REGULATORS OF CYTOKINE RELEASE
  申请人：THE PENN STATE RESEARCH FOUNDATION

  公开号：EP1232169A1

  公开（公告）日：2002-08-21
• US7288273B1
  申请人：——

  公开号：US7288273B1

  公开（公告）日：2007-10-30