trimethylsilyl diallylphosphite | 206055-18-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: trimethylsilyl diallylphosphite
• 英文别名: Bis(prop-2-enyl) trimethylsilyl phosphite；bis(prop-2-enyl) trimethylsilyl phosphite
• CAS: 206055-18-7
• 化学式: C₉H₁₉O₃PSi
• 分子量: 234.307
• InChiKey: MZJBCDJJWKHHCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trimethylsilyl diallylphosphite 在 acid 作用下， 反应 38.0h， 生成 (R)-2-Amino-3-(bis-allyloxy-phosphoryl)-propionic acid
  参考文献：
  名称：

  使用Fmoc-固相合成法将天冬氨酸的膦酸等排异构体整合到肽中

  摘要：

  提出了天冬氨酸的膦酸等排体1的新型Fmoc-衍生物2b的简短合成。掺入图2b为肽使用标准Fmoc固相合成容易地实现。在温和的条件下使用Pd（0）催化进行序列组装后，有效去除烯丙基保护基团可提供高纯度的磷酸肽3a和3b。

  DOI：

  10.1016/s0040-4039(98)00189-0
• 作为产物：
  描述：

  (Z)-trimethylsilyl N-trimethylsilylacetimidate 、 diallyl phosphite 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 trimethylsilyl diallylphosphite
  参考文献：
  名称：

  Synthesis and in vitro evaluation of S-acyl-3-thiopropyl prodrugs of Foscarnet

  摘要：

  A new enzyme-labile group called S-acyl-3-thiopropyl group (SATP) has been synthesized from allylic esters of phosphonate. After demonstration of the enzyme-labile character of the SATP in cellular extracts, it has been introduced onto the phosphonate moiety of PFA (Foscarnet) to obtain potential lipophilic prodrugs. To ponder the lipophilicity of the triesters of PFA, esters of monomethylether of polyethyleneglycols and of thioglycerol were introduced on the PFA carboxylate moiety. The SATP groups were introduced in an attempt to deliver PFA after bioactivation inside the cells. The PFA prodrugs were evaluated in vitro for their activity against human immunodeficiency viruses (HIV-1 and HIV-2). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.017

文献信息

• Convenient synthesis of bisphosphonomethylphosphoric acid
  作者：Val�rie Gagnard、Alain Leydet、V�ronique Barragan、Jean-Louis Montero

  DOI：10.1002/hc.10105

  日期：——

  The reaction of phosgene or triphosgene with trimethylsilyl dialkylphosphites led to bisdialkylphosphonomethyl-dialkylphosphates in good yields. The cleavage of the allyl ester was carried out under mild conditions using the Wilkinson catalyst. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:111–113, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10105

  光气或三光气与亚磷酸三甲基甲硅烷基二烷基酯的反应以良好的产率得到双二烷基膦酰基甲基二烷基磷酸酯。烯丙酯的裂解是在温和条件下使用威尔金森催化剂进行的。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:111–113, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10105
• Synthesis and in vitro evaluation of S-acyl-3-thiopropyl prodrugs of Foscarnet
  作者：Valérie Gagnard、Alain Leydet、Alain Morère、Jean-Louis Montero、Isabelle Lefèbvre、Gilles Gosselin、Christophe Pannecouque、Erick De Clercq

  DOI：10.1016/j.bmc.2004.01.017

  日期：2004.3

  A new enzyme-labile group called S-acyl-3-thiopropyl group (SATP) has been synthesized from allylic esters of phosphonate. After demonstration of the enzyme-labile character of the SATP in cellular extracts, it has been introduced onto the phosphonate moiety of PFA (Foscarnet) to obtain potential lipophilic prodrugs. To ponder the lipophilicity of the triesters of PFA, esters of monomethylether of polyethyleneglycols and of thioglycerol were introduced on the PFA carboxylate moiety. The SATP groups were introduced in an attempt to deliver PFA after bioactivation inside the cells. The PFA prodrugs were evaluated in vitro for their activity against human immunodeficiency viruses (HIV-1 and HIV-2). (C) 2004 Elsevier Ltd. All rights reserved.
• Incorporation of a phosphonic acid isostere of aspartic acid into peptides using Fmoc-solid phase synthesis
  作者：P.A. Lohse、R. Felber

  DOI：10.1016/s0040-4039(98)00189-0

  日期：1998.4

  A short synthesis of a novel Fmoc-derivative 2b of the phosphonic acid isostere 1 of aspartic acid is presented. Incorporation of 2b into peptides was readily achieved using standard Fmoc-solid phase synthesis. Efficient removal of the allyl protecting groups after sequence assembly under mild conditions using Pd(0) catalysis afforded phosphonopeptides 3a and 3b in high purity.

  提出了天冬氨酸的膦酸等排体1的新型Fmoc-衍生物2b的简短合成。掺入图2b为肽使用标准Fmoc固相合成容易地实现。在温和的条件下使用Pd（0）催化进行序列组装后，有效去除烯丙基保护基团可提供高纯度的磷酸肽3a和3b。