(S,E)-4-((tert-butyldimethylsilyl)oxy)pent-2-enoic acid | 1582811-66-2

• 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: (S,E)-4-((tert-butyldimethylsilyl)oxy)pent-2-enoic acid
• 英文别名: (E,4S)-4-[tert-butyl(dimethyl)silyl]oxypent-2-enoic acid
• CAS: 1582811-66-2
• 化学式: C₁₁H₂₂O₃Si
• 分子量: 230.379
• InChiKey: BQYJTPADGKWSNB-FLOXNTQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (S,E)-4-((tert-butyldimethylsilyl)oxy)pent-2-enoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Cis-Double Bond Formation by Thioesterase and Transfer by Ketosynthase in FR901464 Biosynthesis

  摘要：

  Modular polyketide synthases (PKSs) are well known to use ketosynthase (KS)-driven carbon-carbon bond formation, dehydratase-mediated dehydration to form double bonds, and product release by thioesterase (TE), all of which are regarded as the "canonical" roles for most polyketide biosyntheses. FR901464 is biosynthesized by a complex acyltransferase-less PKS system involving a nonterminal TE domain and several mutated KS domains. Here we demonstrate that this TE catalyzes the dehydration of the polyketide intermediate to yield a cis-double bond and a mutated KS transfers the nascent polyketide chain with only a cis-double bond to the downstream acyl carrier protein. These findings not only provide new insights into different enzymatic functions of PKS domains but also suggest an alternative strategy for cis-double bond formation during the polyketide assembly line.

  DOI：

  10.1021/ja500942y
• 作为产物：
  描述：

  (S,E)-ethyl 4-((tert-butyldimethylsilyl)oxy)pent-2-enoate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以1820.2 mg的产率得到(S,E)-4-((tert-butyldimethylsilyl)oxy)pent-2-enoic acid
  参考文献：
  名称：

  Design and synthesis of 4-acetoxypentanamide derivatives of spliceostatin A and their biological evaluation towards prostate cancer treatment

  摘要：

  DOI：

  10.1016/j.bmcl.2023.129333

文献信息

• Oxidation of allylic and benzylic alcohols to aldehydes and carboxylic acids
  作者：Daniel Könning、Tobias Olbrisch、Fanni D. Sypaseuth、C. Christoph Tzschucke、Mathias Christmann

  DOI：10.1039/c4cc01305k

  日期：——

  An oxidation of allylic and benzylic alcohols to the corresponding carboxylic acids is effected by merging a Cu-catalyzed oxidation using O2 as a terminal oxidant with a subsequent chlorite oxidation (Lindgren oxidation). The protocol was optimized to obtain pure products without chromatography or crystallization. Interception at the aldehyde stage allowed for Z/E-isomerization, thus rendering the

  通过将使用O 2作为末端氧化剂的Cu催化的氧化与随后的亚氯酸盐氧化（Lindgren氧化）合并来实现烯丙基和苄醇氧化为相应的羧酸。对该方案进行了优化，以获得无需色谱或结晶的纯净产物。在醛阶段的拦截作用允许Z / E异构化，从而使氧化相对于起始原料的构型立体收敛。
• <i>Cis</i>-Double Bond Formation by Thioesterase and Transfer by Ketosynthase in FR901464 Biosynthesis
  作者：Hai-Yan He、Man-Cheng Tang、Feng Zhang、Gong-Li Tang

  DOI：10.1021/ja500942y

  日期：2014.3.26

  Modular polyketide synthases (PKSs) are well known to use ketosynthase (KS)-driven carbon-carbon bond formation, dehydratase-mediated dehydration to form double bonds, and product release by thioesterase (TE), all of which are regarded as the "canonical" roles for most polyketide biosyntheses. FR901464 is biosynthesized by a complex acyltransferase-less PKS system involving a nonterminal TE domain and several mutated KS domains. Here we demonstrate that this TE catalyzes the dehydration of the polyketide intermediate to yield a cis-double bond and a mutated KS transfers the nascent polyketide chain with only a cis-double bond to the downstream acyl carrier protein. These findings not only provide new insights into different enzymatic functions of PKS domains but also suggest an alternative strategy for cis-double bond formation during the polyketide assembly line.
• Design and synthesis of 4-acetoxypentanamide derivatives of spliceostatin A and their biological evaluation towards prostate cancer treatment
  作者：Satoru Hirabayashi、Yuko Tsuyuguchi、Yue Li、Noriko Ohta、Yusuke Yoshikawa、Bangzhong Lin、Megumi Fumimoto、Kazuto Nunomura、Takeyuki Suzuki、Junichi Haruta、Keisuke Nimura、Mitsuhiro Arisawa

  DOI：10.1016/j.bmcl.2023.129333

  日期：2023.7