methyl (4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-2-ynoate | 753016-51-2

• 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: methyl (4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-2-ynoate
• CAS: 753016-51-2
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: MFMPPDHHOJGKFR-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-2-ynoate 在 Lindlar's catalyst Dowex 50W X₈ 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 43.0h， 生成 ((2R,3S)-6-Isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-methanol
  参考文献：
  名称：

  First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination

  摘要：

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.

  DOI：

  10.1021/ol049219z
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 、 正丁基锂 、 三苯基膦 作用下， 生成 methyl (4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-2-ynoate
  参考文献：
  名称：

  A practical synthesis of (−)-kazusamycin A (revised)

  摘要：

  We describe herein a stereo-controlled and practical synthesis of three key building blocks, namely Segment AB', Segment D, and Segment E' needed for the total synthesis of (-)-kazusamycin A. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.029

文献信息

• Aplyronine A, a potent antitumor macrolide of marine origin, and the congeners aplyronines B and C: isolation, structures, and bioactivities
  作者：Makoto Ojika、Hideo Kigoshi、Yoshifumi Yoshida、Takeshi Ishigaki、Masanori Nisiwaki、Itaru Tsukada、Masayuki Arakawa、Hisao Ekimoto、Kiyoyuki Yamada

  DOI：10.1016/j.tet.2007.02.011

  日期：2007.4

  isolated from the sea hare Aplysia kurodai together with the congeners aplyronines B (3) and C (4). The absolute stereostructure of aplyronine A (2) was determined by the instrumental analysis (mainly NMR and MS) and the enantioselective synthesis of the fragments obtained from chemical degradation of aplyronine A (2). The structures of aplyronines B (3) and C (4) were also elucidated. Cytotoxicity and

  从海兔Aplysia kurodai中分离到了一种有效的抗肿瘤大环内酯-Aplyronine A（2），以及同类的aplyronines B（3）和C（4）。通过仪器分析（主要是NMR和MS）和对苯丙氨酸A（2）的化学降解获得的片段的对映选择性合成，确定了苯丙氨酸A（2）的绝对立体结构。还阐明了鸭绿素B（3）和C（4）的结构。肾上腺素A（2）的细胞毒性和抗肿瘤活性进行了评估。
• Studies on the stereochemistry of aplyronine A: Determination of the stereochemistry of the C21C34 fragment
  作者：Makoto Ojika、Hideo Kigoshi、Takeshi Ishigaki、Masanori Nisiwaki、Itaru Tsukada、Kazuhiro Mizuta、Kiyoyuki Yamada

  DOI：10.1016/s0040-4039(00)61370-9

  日期：1993.1

  The absolute stereochemistry of the C21C34 fragment 2 of aplyronine A (1), a potent antitumor substance of marine origin, was determined by enantioselective synthesis.

  通过对映选择性合成确定了aplyronine A（1）（一种有效的海洋来源抗肿瘤物质）的C21C34片段2的绝对立体化学。
• Design, synthesis, and evaluation of novel kazusamycin A derivatives as potent antitumor agents
  作者：Ryoichi Ando、Yusaku Amano、Hideo Nakamura、Noriyoshi Arai、Isao Kuwajima

  DOI：10.1016/j.bmcl.2006.03.056

  日期：2006.6

  Novel kazusamycin A derivatives were designed in the viewpoint of decrease of reactivity at the alpha,beta-unsaturated delta-lactone moiety against Michael-type addition. Although 25-30 steps were required for the synthesis of each compound, their syntheses were achieved. Cytotoxicity against HPAC cell line was evaluated, and two of them exhibited comparable potency to kazusamycin A. Hepatic toxicity of these designed compounds was much lower than that of kazusamycin A. (c) 2006 Elsevier Ltd. All rights reserved.
• A practical synthesis of (−)-kazusamycin A (revised)
  作者：Shengfeng Zhou、Huaxiang Chen、Wensheng Liao、Shu-Hui Chen、Ge Li、Ryoichi Ando、Isao Kuwajima

  DOI：10.1016/j.tetlet.2005.07.029

  日期：2005.9

  We describe herein a stereo-controlled and practical synthesis of three key building blocks, namely Segment AB', Segment D, and Segment E' needed for the total synthesis of (-)-kazusamycin A. (c) 2005 Elsevier Ltd. All rights reserved.
• First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination
  作者：Noriyoshi Arai、Noriko Chikaraishi、Satoshi Omura、Isao Kuwajima

  DOI：10.1021/ol049219z

  日期：2004.8.1

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.