4-triethylsilyloxy-4-methylpentanoic acid | 383397-31-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-triethylsilyloxy-4-methylpentanoic acid
• 英文别名: 4-triethylsilyloxy-4-methyl-pentanoic acid；4-Methyl-4-triethylsilyloxypentanoic acid
• CAS: 383397-31-7
• 化学式: C₁₂H₂₆O₃Si
• 分子量: 246.422
• InChiKey: XURIBPUOSXFZSB-UHFFFAOYSA-N

物化性质

• 沸点：
  308.2±25.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-triethylsilyloxy-4-methylpentanoic acid 在 palladium on activated charcoal 吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 四(三苯基膦)钯 、 氢气 、 双氧水 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.25h， 生成 tert-butyl N-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-1-[(2R)-2-hydroxy-4-methyl-4-triethylsilyloxypentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]-methylamino]-3-methylbutanoyl]-methylamino]propanoyl]amino]carbamate
  参考文献：
  名称：

  Probing Host-Selective Phytotoxicity:  Synthesis of Destruxin B and Several Natural Analogues

  摘要：

  The syntheses of the host-selective phytotoxin destruxin B [cyclo(beta Ala-Hmp-Pro-Ile-MeVal-MeAla), Hmp = (2R)-2-hydroxy-4-methylpentanoic acid], and the closely related natural analogues homodestruxin B (MeVal --> MeIle), desmethyldestruxin B (MeVal --> Val), hydroxydestruxin B (Hmp --> Dhmp, Dhmp = (2R)-2,4-dihydroxy-4-methylpentanoic acid), and hydroxyhomodestruxin B (MeVal --> MeIle, Hmp-Dhmp) are described. In each case, the MeAla-beta Ala linkage was formed by cyclization and the precursor linear hexadepsipeptides were formed by condensing two three-residue fragments. Radiolabeled samples of destruxin B, homodestruxin B, and hydroxydestruxin B were prepared by coupling [3-C-14]-beta -alanine to the appropriate pentadepsipeptide followed by cyclization. A noteworthy feature of the synthesis involves the novel use of a Boc-hydrazide protecting group on dipeptides with a C-terminal N-methylalanine residue to inhibit the otherwise facile dioxopiperazine formation during peptide coupling.

  DOI：

  10.1021/jo015953+
• 作为产物：
  描述：

  4-hydroxy-4-methyl-valeric acid 在 2,6-二甲基吡啶 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 19.75h， 生成 4-triethylsilyloxy-4-methylpentanoic acid
  参考文献：
  名称：

  Probing Host-Selective Phytotoxicity:  Synthesis of Destruxin B and Several Natural Analogues

  摘要：

  The syntheses of the host-selective phytotoxin destruxin B [cyclo(beta Ala-Hmp-Pro-Ile-MeVal-MeAla), Hmp = (2R)-2-hydroxy-4-methylpentanoic acid], and the closely related natural analogues homodestruxin B (MeVal --> MeIle), desmethyldestruxin B (MeVal --> Val), hydroxydestruxin B (Hmp --> Dhmp, Dhmp = (2R)-2,4-dihydroxy-4-methylpentanoic acid), and hydroxyhomodestruxin B (MeVal --> MeIle, Hmp-Dhmp) are described. In each case, the MeAla-beta Ala linkage was formed by cyclization and the precursor linear hexadepsipeptides were formed by condensing two three-residue fragments. Radiolabeled samples of destruxin B, homodestruxin B, and hydroxydestruxin B were prepared by coupling [3-C-14]-beta -alanine to the appropriate pentadepsipeptide followed by cyclization. A noteworthy feature of the synthesis involves the novel use of a Boc-hydrazide protecting group on dipeptides with a C-terminal N-methylalanine residue to inhibit the otherwise facile dioxopiperazine formation during peptide coupling.

  DOI：

  10.1021/jo015953+

文献信息

• 9,10-세코프레그난 유도체 및 의약
  申请人：NIPPON SHINYAKU CO., LTD. 니뽄 신야쿠 가부시키가이샤(519980958747)

  公开号：KR20150054011A

  公开（公告）日：2015-05-19

  본 발명은 우수한 비타민 D3 활성을 가지면서, 전신성 칼슘 대사에 미치는 영향이 적은 신규의 유용한 비타민 D3 유도체를 제공하는 것을 목적으로 한다. 본 발명으로서, 하기 화학식 1로 표시되는 9,10-세코프레그난 유도체 및 그것을 유효 성분으로서 함유하는 의약 조성물을 들 수 있다. 화학식 1 중 Y는 (1) 단결합, (2) 알킬렌, (3) 알케닐렌 또는 (4) 페닐렌을 나타내고, R, R는 동일하거나 또는 다르며, (1) 수소, (2) 알킬 또는 (3) 시클로알킬을 나타내거나 또는 R, R가 인접한 탄소 원자와 함께 시클로알킬을 나타내고, R은 수소 또는 메틸을 나타내며, Z는 (1) 수소, (2) 히드록시 또는 (3) -NRR를 나타낸다.

  本发明旨在提供一种具有优异的维生素D3活性，对全身钙代谢影响较小的新型有用的维生素D3衍生物。根据本发明，可以提供如下所示的化学式1所示的9,10-脱环孕甾烷衍生物以及含有其作为有效成分的药物组合物。在化学式1中，Y代表(1) 单键，(2) 烷基，(3) 烯烃基或(4) 苯基，R，R相同或不同，(1) 氢，(2) 烷基或(3) 环烷基，或R，R与相邻碳原子一起表示环烷基，R表示氢或甲基，Z代表(1) 氢，(2) 羟基或(3) -NRR。
• WO2006/59768
  申请人：——

  公开号：——

  公开（公告）日：——
• 9,10-SECOPREGNANE DERIVATIVE AND PHARMACEUTICAL
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP2025667B1

  公开（公告）日：2016-08-10
• Metabolism of the Host-Selective Toxins Destruxin B and Homodestruxin B:  Probing a Plant Disease Resistance Trait
  作者：M. Soledade C. Pedras、Irina. L. Zaharia、Yuanzhu Gai、Kevin C. Smith、Dale E. Ward

  DOI：10.1021/ol991042z

  日期：1999.11.1

  [GRAPHICS]Metabolism of the host-selective toxins destruxin B (1) and homodestruxin B (2) by plants resistant and susceptible to Alternaria blackspot (caused by the fungal pathogen Alternaria brassicae (Berk,) Sacc,) was established using synthetic radiolabeied compounds. The toxins are transformed into the less phytotoxic hydroxydestruxins 3 and 4. The rate of metabolic transformation was correlated with the plant's disease resistance, i.e., significantly faster rates were observed for plants resistant to the pathogen, Efficient syntheses of 1, 2, 3, and 4 are described.
• Probing Host-Selective Phytotoxicity:  Synthesis of Destruxin B and Several Natural Analogues
  作者：Dale E. Ward、Yuanzhu Gai、Ryszard Lazny、M. Soledade C. Pedras

  DOI：10.1021/jo015953+

  日期：2001.11.1

  The syntheses of the host-selective phytotoxin destruxin B [cyclo(beta Ala-Hmp-Pro-Ile-MeVal-MeAla), Hmp = (2R)-2-hydroxy-4-methylpentanoic acid], and the closely related natural analogues homodestruxin B (MeVal --> MeIle), desmethyldestruxin B (MeVal --> Val), hydroxydestruxin B (Hmp --> Dhmp, Dhmp = (2R)-2,4-dihydroxy-4-methylpentanoic acid), and hydroxyhomodestruxin B (MeVal --> MeIle, Hmp-Dhmp) are described. In each case, the MeAla-beta Ala linkage was formed by cyclization and the precursor linear hexadepsipeptides were formed by condensing two three-residue fragments. Radiolabeled samples of destruxin B, homodestruxin B, and hydroxydestruxin B were prepared by coupling [3-C-14]-beta -alanine to the appropriate pentadepsipeptide followed by cyclization. A noteworthy feature of the synthesis involves the novel use of a Boc-hydrazide protecting group on dipeptides with a C-terminal N-methylalanine residue to inhibit the otherwise facile dioxopiperazine formation during peptide coupling.