methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate | 223930-86-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate
• 英文别名: methyl 3-(4-phenylmethoxyphenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropanoate
• CAS: 223930-86-7
• 化学式: C₃₁H₃₆O₁₃
• 分子量: 616.619
• InChiKey: MCICRCSYOAXCRD-HFRRIYTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate
  参考文献：
  名称：

  叶片运动的生物学意义，一种使用封闭叶的合成抑制剂的方法

  摘要：

  在豆科植物中已经广泛观察到了夜蛾叶片运动，其是根据昼夜节律的叶子的折叠和打开运动。尽管自亚历山大大帝时代以来就已知道这种运动，但问题“为什么豆科植物会睡觉？” 一直困扰着许多研究夜市的科学家。我们已经揭示，夜蛾的叶片运动通过使用合成的叶片运动抑制剂抑制叶片运动对于豆科植物的生存是必不可少的。豆科植物将枯萎而无夜蛾死亡。我们的结果提供了一个历史线索的重要线索：“为什么豆科植物会睡觉？”

  DOI：

  10.1016/s0040-4039(02)01770-7
• 作为产物：
  描述：

  4-羟基苯基乳酸甲酯 在 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate
  参考文献：
  名称：

  Syntheses and novel bioactivities of artificial leaf-opening substances of Lespedeza cuneata G. Don, designed for the bioorganic studies of nyctinasty

  摘要：

  Potassium lespedezate (1) is the leaf-opening substance of a nyctinastic plant, Lespedeza cuneata G.Don. We have synthesized two sugar-derivatives of 1, potassium galactolespedezate (4) and mannolespedezate (6). Both 4 and 6 were quite effective for the leaf-opening of Cassia. mimosoides at 8 x 10(-7) M, as strong as 1. However, 1 kept the leaf open only for a few days; on the other hand. 4 and 6 kept the leaf open after a week at that concentration. Additionally, remarkable difference was observed in the rate of enzymatic hydrolysis of natural and artificial leaf-opening sustance by using commercially available beta-glucosidase Therefore, 4 and 6 would not be hydrolized in the plant body, and are potentially useful molecular probes for the studies of the control of the nyctinastic leaf-movement by a biological clock. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00618-3

文献信息

• Sugar-derivatives of potassium lespedezate, artificial leaf-opening substances of Lespedeza cuneata G. Don, designed for the bioorganic studies of nyctinasty
  作者：Minoru Ueda、Yoshiyuki Sawai、Shosuke Yamamura

  DOI：10.1016/s0040-4039(99)00602-4

  日期：1999.5

  Potassium lespedezate (1) is the leaf-opening substance of a nyctinastic plant, Lespedeza cuneata G. Don. We synthesized two sugar-derivatives of 1, potassium galactolespedezate (2) and mannoisolespedezate (3). Both 2 and 3 were quite effective for the leaf-opening of L. cuneata. at 8 x 10(-7) M, as strong as 1. However, 1 kept the leaf open only for a few days; on the other hand, 2 and 3 kept the leaf open after a week at that concentration. Thus it is assumed that 2 and 3 could not be hydrolyzed by beta-glucosidase in the plant body, and are therefore potentially useful molecular probes for the studies of the control of the nyctinastic leaf-movement by a biological clock. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Syntheses and novel bioactivities of artificial leaf-opening substances of Lespedeza cuneata G. Don, designed for the bioorganic studies of nyctinasty
  作者：Minoru Ueda、Yoshiyuki Sawai、Shosuke Yamamura

  DOI：10.1016/s0040-4020(99)00618-3

  日期：1999.9

  Potassium lespedezate (1) is the leaf-opening substance of a nyctinastic plant, Lespedeza cuneata G.Don. We have synthesized two sugar-derivatives of 1, potassium galactolespedezate (4) and mannolespedezate (6). Both 4 and 6 were quite effective for the leaf-opening of Cassia. mimosoides at 8 x 10(-7) M, as strong as 1. However, 1 kept the leaf open only for a few days; on the other hand. 4 and 6 kept the leaf open after a week at that concentration. Additionally, remarkable difference was observed in the rate of enzymatic hydrolysis of natural and artificial leaf-opening sustance by using commercially available beta-glucosidase Therefore, 4 and 6 would not be hydrolized in the plant body, and are potentially useful molecular probes for the studies of the control of the nyctinastic leaf-movement by a biological clock. (C) 1999 Elsevier Science Ltd. All rights reserved.
• The biological significance of leaf-movement, an approach using a synthetic inhibitor of leaf-closure
  作者：Minoru Ueda、Takanori Sugimoto、Yoshiyuki Sawai、Shosuke Yamamura

  DOI：10.1016/s0040-4039(02)01770-7

  日期：2002.10

  sleep?’ has always puzzled many scientists studying nyctinasty. We have revealed that nyctinastic leaf-movement is essential for the survival of leguminous plants by inhibiting leaf-movement using synthetic leaf movement inhibitor. Leguminous plant will wither and die without nyctinasty. Our result gives an important clue for the historic mystery, ‘Why does the leguminous plant sleep?’

  在豆科植物中已经广泛观察到了夜蛾叶片运动，其是根据昼夜节律的叶子的折叠和打开运动。尽管自亚历山大大帝时代以来就已知道这种运动，但问题“为什么豆科植物会睡觉？” 一直困扰着许多研究夜市的科学家。我们已经揭示，夜蛾的叶片运动通过使用合成的叶片运动抑制剂抑制叶片运动对于豆科植物的生存是必不可少的。豆科植物将枯萎而无夜蛾死亡。我们的结果提供了一个历史线索的重要线索：“为什么豆科植物会睡觉？”