[(3E)-hexa-3,5-dienyl] N-[(3R)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-3-hydroxypentyl]carbamate | 743469-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(3E)-hexa-3,5-dienyl] N-[(3R)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-3-hydroxypentyl]carbamate
• CAS: 743469-63-8
• 化学式: C₃₃H₃₉NO₆
• 分子量: 545.676
• InChiKey: MHQXWUTXBYVGLC-DACCQFILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 [(3E)-hexa-3,5-dienyl] N-[(3R)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-3-hydroxypentyl]carbamate 在 二氯特诺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到[(3E)-hexa-3,5-dienyl] N-[(3R)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-3-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxypentyl]carbamate
  参考文献：
  名称：

  Diels−Alder Bioconjugation of Diene-Modified Oligonucleotides

  摘要：

  In an effort to offer complementary technology for covalent biomolecule modification (bioconjugation), we have developed a method that exploits the aqueous acceleration of Diels-Alder reactions for this purpose. Three different diene phosphoramidite reagents have been synthesized that enable diene modification of synthetic oligonucleotides prepared by the phosphoramidite method. Clean and efficient Diels-Alder cycloaddition of these diene oligonucleotides with maleimide dieneophiles was carried out, and the labeled oligonucleotide bioconjugates were characterized by HPLC and electrospray mass spectrometry. Dieneophile stoichiometry, temperature, and pH are all parameters that were shown to influence the efficiency of the process.

  DOI：

  10.1021/jo0100190
• 作为产物：
  描述：

  山梨酸 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 生成 [(3E)-hexa-3,5-dienyl] N-[(3R)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-3-hydroxypentyl]carbamate
  参考文献：
  名称：

  COVALENT MODIFICATION AND SURFACE IMMOBILIZATION OF NUCLEIC ACIDS VIA THE DIELS-ALDER BIOCONJUGATION METHOD

  摘要：

  The importance of chemically modified and surface immobilized nucleic acids has inspired the development of a wide variety of complementary techniques for covalent oligonucleotide preparation and immobilization. We are developing technology based on the use of a Diels-Alder reaction for accomplishing the covalent modification of oligonucleotides. Reported herein is preliminary progress toward the establishment of robust reagents for introducing the reactive functionality, as well as studies employing the BIACORE system to demonstrate surface immobilization by the method.

  DOI：

  10.1081/ncn-100002332

文献信息

• COVALENT MODIFICATION AND SURFACE IMMOBILIZATION OF NUCLEIC ACIDS VIA THE DIELS-ALDER BIOCONJUGATION METHOD
  作者：Gregory M. Husar、Dominick J. Anziano、Michael Leuck、David P. Sebesta

  DOI：10.1081/ncn-100002332

  日期：2001.3.31

  The importance of chemically modified and surface immobilized nucleic acids has inspired the development of a wide variety of complementary techniques for covalent oligonucleotide preparation and immobilization. We are developing technology based on the use of a Diels-Alder reaction for accomplishing the covalent modification of oligonucleotides. Reported herein is preliminary progress toward the establishment of robust reagents for introducing the reactive functionality, as well as studies employing the BIACORE system to demonstrate surface immobilization by the method.
• Diels−Alder Bioconjugation of Diene-Modified Oligonucleotides
  作者：Kenneth W. Hill、Jon Taunton-Rigby、Jeffrey D. Carter、Eric Kropp、Kurt Vagle、Wolfgang Pieken、Danny P. C. McGee、Gregory M. Husar、Michael Leuck、Dominic J. Anziano、David P. Sebesta

  DOI：10.1021/jo0100190

  日期：2001.8.1

  In an effort to offer complementary technology for covalent biomolecule modification (bioconjugation), we have developed a method that exploits the aqueous acceleration of Diels-Alder reactions for this purpose. Three different diene phosphoramidite reagents have been synthesized that enable diene modification of synthetic oligonucleotides prepared by the phosphoramidite method. Clean and efficient Diels-Alder cycloaddition of these diene oligonucleotides with maleimide dieneophiles was carried out, and the labeled oligonucleotide bioconjugates were characterized by HPLC and electrospray mass spectrometry. Dieneophile stoichiometry, temperature, and pH are all parameters that were shown to influence the efficiency of the process.