ethyl (R)-4-(carboxyamino)-6-methyl-3-oxoheptanoate 4-tert-butyl ester | 114155-31-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl (R)-4-(carboxyamino)-6-methyl-3-oxoheptanoate 4-tert-butyl ester
• 英文别名: (R)-ethyl 4-(tert-butoxycarbonylamino)-6-methyl-3-oxoheptanoate；N-tert-butoxycarbonyl-D-leucylacetate；ethyl (4R)-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxoheptanoate
• CAS: 114155-31-6
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: UJWVZXIMCGERRM-LLVKDONJSA-N

物化性质

• 沸点：
  388.9±22.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (R)-4-(carboxyamino)-6-methyl-3-oxoheptanoate 4-tert-butyl ester 在 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 三氟乙酸 为溶剂， 反应 3.0h， 生成 D-亮氨酸
  参考文献：
  名称：

  Isolation and Structures of Nostopeptolides A1, A2 and A3 from the Cyanobacterium Nostoc sp. GSV224

  摘要：

  The isolation and total structure determinations of nostopeptolides A1 (1), A2 (2) and A3 (3) are described. These cyclic depsipeptides, which are devoid of cytotoxic, antifungal and inhibition of protease activities, are characteristic constituents of the cryptophycin-producing cyanobacterium Nostoc sp. GSV224. Structure elucidation by NMR analysis was made more challenging by the existence of each nostopeptolide in three conformations. One-dimensional TOCSY experiments proved to be very useful in isolating and identifying the nine amino acid residues and the butyryl group in each compound. The absolute stereochemistries of 1-3 were determined by comparing the amino acids in the acid hydrolyzates directly with authentic standards. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00764-x
• 作为产物：
  描述：

  D-亮氨酸 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 15.67h， 生成 ethyl (R)-4-(carboxyamino)-6-methyl-3-oxoheptanoate 4-tert-butyl ester
  参考文献：
  名称：

  双氢精蛋白的合成研究。III：他汀和异他汀立体异构体的合成

  摘要：

  研究了还原β-酮酸酯前体导致几种他汀类和异他汀类立体异构体的立体选择性。结果，设计了一种短的且高度立体选择性的途径，以产生在二氢肌宁中（3S，4R，5S）-异冰片碱中的异他汀的异构体。

  DOI：

  10.1016/s0040-4020(01)85979-2

文献信息

• Total synthesis of bicyclic depsipeptides spiruchostatins C and D and investigation of their histone deacetylase inhibitory and antiproliferative activities
  作者：Koichi Narita、Yurie Fukui、Yui Sano、Takao Yamori、Akihiro Ito、Minoru Yoshida、Tadashi Katoh

  DOI：10.1016/j.ejmech.2012.12.023

  日期：2013.2

  The bicyclic depsipeptide histone deacetylase (HDAC) inhibitors spiruchostatins C and D were synthesized for the first time in a highly convergent and unified manner. The method features the amide coupling of a d-leucine–d-cysteine- or d-valine–d-cysteine-containing segment with a d-alanine- or d-valine-containing segment to directly assemble the corresponding seco-acids, key precursors of macrolactonization

  双环二肽组蛋白去乙酰化酶（HDAC）抑制剂spiruchostatins C和D首次以高度收敛和统一的方式合成。该方法采用了酰胺的耦合d -leucine- d -cysteine-或d -valine- d段与含半胱氨酸- d -alanine-或d含缬氨酸段直接组装相应的开环-酸，大内酯化的关键前体。合成的大肽肽的HDAC抑制分析和细胞生长抑制分析确定了螺旋藻抑素A–D与临床批准的大肽肽FK228（romidepsin）相比的效力顺序。揭示了结构-活性关系（SAR）的新颖方面。
• Synthetic studies of didemnins. II. Approaches to statine diastereomers
  作者：Bruce D Harris、K.L Bhat、Madeleine M Joullie'

  DOI：10.1016/s0040-4039(00)96222-1

  日期：1987.1

  A short and efficient route to (3S,4R)-statine has been developed in connection with synthetic studies toward didemnins A,B and C.

  与针对双嘧达明A，B和C的合成研究相结合，已开发出一种短而有效的（3S，4R）-Statine途径。
• HARRIS, BRUCC D.;JOULLIE, MADELEINE M., TETRAHEDRON, 44,(1988) N 12, 3489-3500
  作者：HARRIS, BRUCC D.、JOULLIE, MADELEINE M.

  DOI：——

  日期：——
• HARRIS, BRUCE D.;BHAT, K. L.;JOULLIE, MADELEINE M., TETRAHEDRON LETT., 28,(1987) N 25, 2837-2840
  作者：HARRIS, BRUCE D.、BHAT, K. L.、JOULLIE, MADELEINE M.

  DOI：——

  日期：——
• Synthetic studies of didemnins. III
  作者：Bruce D. Harris、Madeleine M. Joullié

  DOI：10.1016/s0040-4020(01)85979-2

  日期：——

  The stereoselectivity of the reduction of β-keto ester precursors leading to several stereoisomers of statine and isostatine was investigated. As a result, a short and highly stereoselective route to the isomar of isostatine found in the didemnins, (3S,4R,5S)-isostaline, was devised.

  研究了还原β-酮酸酯前体导致几种他汀类和异他汀类立体异构体的立体选择性。结果，设计了一种短的且高度立体选择性的途径，以产生在二氢肌宁中（3S，4R，5S）-异冰片碱中的异他汀的异构体。