methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate | 478701-19-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate
• 英文别名: methyl (Z)-3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-6-(hydroxymethyl)oxan-2-yl]oxyprop-2-enoate
• CAS: 478701-19-8
• 化学式: C₄₀H₇₆O₉Si₄
• 分子量: 813.38
• InChiKey: RACYDLMZACOWDW-ZCFFHDTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.49
• 重原子数：
  53.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以60%的产率得到methyl (Z)-3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-6-formyloxan-2-yl]oxyprop-2-enoate
  参考文献：
  名称：

  Detection of 210 kDa receptor protein for a leaf-movement factor by using novel photoaffinity probes

  摘要：

  Circadian rhythmic plant leaf-movement, called nyctinasty, is controlled by a time-course change in the internal concentration of the leaf-movement factor in the plant body. We revealed that specific binding proteins (210 and 180 kDa) for the leaf-movement factor, potassium lespedezate (1), are contained in the plasma membrane of the plant motor cell by using novel synthetic photoaffinity probes. These proteins are localized on the motor cell in the plant body, and would be potential receptors for the leaf-movement factor to control the leaf-movement. Our study is a rare successful result of the detection of membrane receptors by using a synthetic photoaffinity probe designed on a biologically active natural product. And these results also advance a guideline for probe design towards successful photoaffinity labeling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.022
• 作为产物：
  描述：

  methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate 在 palladium dihydroxide 、 4 A molecular sieve 吡啶 、 2,6-二甲基吡啶 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate
  参考文献：
  名称：

  Detection of 210 kDa receptor protein for a leaf-movement factor by using novel photoaffinity probes

  摘要：

  Circadian rhythmic plant leaf-movement, called nyctinasty, is controlled by a time-course change in the internal concentration of the leaf-movement factor in the plant body. We revealed that specific binding proteins (210 and 180 kDa) for the leaf-movement factor, potassium lespedezate (1), are contained in the plasma membrane of the plant motor cell by using novel synthetic photoaffinity probes. These proteins are localized on the motor cell in the plant body, and would be potential receptors for the leaf-movement factor to control the leaf-movement. Our study is a rare successful result of the detection of membrane receptors by using a synthetic photoaffinity probe designed on a biologically active natural product. And these results also advance a guideline for probe design towards successful photoaffinity labeling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.022