[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(3,4,5-trimethoxybenzoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 3,4,5-trimethoxybenzoate | 157485-54-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: [(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(3,4,5-trimethoxybenzoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 3,4,5-trimethoxybenzoate
• CAS: 157485-54-6
• 化学式: C₃₄H₃₈O₁₄
• 分子量: 670.667
• InChiKey: YSDMESBIEUSJBT-QVYQDBIISA-N

物化性质

• 沸点：
  704.8±60.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(3,4,5-trimethoxybenzoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 3,4,5-trimethoxybenzoate 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 (S)-6,6'-dihydroxymethyl-2,2',3,3',4,4'-hexamethoxy-1,1'-biphenyl
  参考文献：
  名称：

  An unexpected intermolecular chiral biaryl coupling reaction induced by a hypervalent iodine(III) reagent: synthesis of potential precursor for ellagitannin

  摘要：

  一种新型的酚碘（III）双（三氟乙酸盐）（PIFA）诱导的分子间手性双芳基偶联反应已经成功完成，采用α-D-葡萄糖衍生物作为手性模板。

  DOI：

  10.1039/a809680e
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 、 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以78%的产率得到[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(3,4,5-trimethoxybenzoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 3,4,5-trimethoxybenzoate
  参考文献：
  名称：

  A Rapid Total Synthesis of an Ellagitannin

  摘要：

  The ellagitannins are galloyl esters of glucose that contain at least one chiral biaryl (digalloyl) subunit. Included in this family are the tellimagrandins (1-3). The first asymmetric synthesis of (S)-4,4',5,5',6,6'-hexamethoxy-2,2'-diphenic acid, a ubiquitous subunit in ellagitannins, is reported by utilization of an intermolecular oxazoline-mediated asymmetric Ullmann coupling. Attachment of this acid to an appropriate glucose core resulted in the synthesis of an ellagitannin.

  DOI：

  10.1021/jo00088a046

文献信息

• An unexpected intermolecular chiral biaryl coupling reaction induced by a hypervalent iodine(III) reagent: synthesis of potential precursor for ellagitannin
  作者：Mitsuhiro Arisawa、Saori Utsumi、Makiko Nakajima、Namakkal G. Ramesh、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1039/a809680e

  日期：——

  A novel phenyliodine(III) bis(trifluoroacetate) (PIFA)-induced intermolecular chiral biaryl coupling reaction has been accomplished using α-D-glucose derivatives as chiral templates.

  一种新型的酚碘（III）双（三氟乙酸盐）（PIFA）诱导的分子间手性双芳基偶联反应已经成功完成，采用α-D-葡萄糖衍生物作为手性模板。
• A Rapid Total Synthesis of an Ellagitannin
  作者：Todd D. Nelson、A. I. Meyers

  DOI：10.1021/jo00088a046

  日期：1994.5

  The ellagitannins are galloyl esters of glucose that contain at least one chiral biaryl (digalloyl) subunit. Included in this family are the tellimagrandins (1-3). The first asymmetric synthesis of (S)-4,4',5,5',6,6'-hexamethoxy-2,2'-diphenic acid, a ubiquitous subunit in ellagitannins, is reported by utilization of an intermolecular oxazoline-mediated asymmetric Ullmann coupling. Attachment of this acid to an appropriate glucose core resulted in the synthesis of an ellagitannin.