methyl 2-(6'-O-benzyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate | 478701-10-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: methyl 2-(6'-O-benzyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate
• 英文别名: methyl 3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoate
• CAS: 478701-10-9
• 化学式: C₄₇H₈₄O₉Si₄
• 分子量: 905.521
• InChiKey: LVHXPRYHUZIMOX-YWDKSFABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.28
• 重原子数：
  60.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(6'-O-benzyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate
  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：

  2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide 在 4 A molecular sieve 2,6-二甲基吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 methyl 2-(6'-O-benzyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate
  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

文献信息

• Syntheses of novel photoaffinity probes for bioorganic studies on nyctinasty of leguminous plants
  作者：Takanori Sugimoto、Tomohiko Fujii、Yasumaru Hatanaka、Shosuke Yamamura、Minoru Ueda

  DOI：10.1016/s0040-4039(02)01460-0

  日期：2002.9

  Novel and non-radioactive photoaffinity probes (1 and 2) for the bioorganic Study of nyctinasty are designed and synthesized based on potassium isolespedezate (3), which induce leaf-opening against the leaf of Cassia mimosoides L. These probes bear a trifluoromethyldiazirine or diazophenyl group for photoaffinity and a biotin Subunit for affinity chromatography and chemiluminescent detection. Probes (1 and 2) showed leaf-opening activity at 5x10(-5) mol/L with leaves of C. mimosoides; thus, they would be an important tool for the identification of a receptor protein for 3. (C) 2002 Elsevier Science Ltd. All rights reserved.