5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde | 206260-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde
• 英文别名: (1'R,2R,5R)-(1'-methoxymethoxytridecyl)tetrahydrofuran-2-carbaldehyde；(2R,5R)-5-[(1R)-1-(methoxymethoxy)tridecyl]oxolane-2-carbaldehyde
• CAS: 206260-14-2
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: GUITXQVNDLZMLO-VAMGGRTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde 在 4 A molecular sieve 4-二甲氨基吡啶 、 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 72.5h， 生成 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Gigantecin:  Exploiting the Asymmetric Glycolate Aldol Reaction

  摘要：

  The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide addition is used to establish the C17 stereocenter.

  DOI：

  10.1021/ja0455852
• 作为产物：
  描述：

  Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]- 在 palladium on activated charcoal N-甲基吡咯烷酮 、 甲醇 、 4-二甲氨基吡啶 、 锂硼氢 、 ruthenium carbene complex 、 草酰氯 、 potassium tert-butylate 、 氢气 、 三甲基乙酰氯 、 四氯化钛 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 100.25h， 生成 5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Gigantecin:  Exploiting the Asymmetric Glycolate Aldol Reaction

  摘要：

  The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide addition is used to establish the C17 stereocenter.

  DOI：

  10.1021/ja0455852

文献信息

• Total Synthesis of a Nonclassical Bioactive Acetogenin, (+)-Muconin
  作者：Wen-Qian Yang、Takeshi Kitahara

  DOI：10.1016/s0040-4020(00)00033-8

  日期：2000.3

  A convergent total synthesis of the tetrahydropyran-bearing acetogenin (+)-muconin 1 is described. All five chiral building blocks 7, 9, 17, 21, and 29 were prepared from d-glutamic acid, respectively. Four out of them were used to furnish the alkyne 16 and the iodoalkyne 33, respectively, and palladium(0)-mediated cross-coupling of alkynes 16 and 33, followed by hydrogenation, afforded 36. Simultaneous

  描述了具有四氢吡喃的产乙酸原蛋白（+）-粘蛋白1的会聚全合成。所有五个手性构建块7，9，17，21，和29，从d谷氨酸分别制备。其中四个用于分别提供炔烃16和碘代炔烃33，以及钯（0）介导的炔烃16和33的交叉偶联，然后氢化，得到36。同时用BF 3 Et 2对36个MOM和TBS基团同时脱保护O在存在Me 2 S的情况下提供（+）-muconin 1。
• Stereocontrolled synthesis of the tetrahydrofuran unit of annonaceous acetogenins
  作者：Keqiang Li、Shikha Vig、Fatih.M. Uckun

  DOI：10.1016/s0040-4039(98)00188-9

  日期：1998.4

  has been prepared from benzyl (R)-(−)-glycidyl ether using a 10-step synthetic scheme in a stereocontrolled fashion. Compound 8 is a highly useful synthon for the synthesis of mono- and di- THF acetogenins. This new synthetic approach can also be applied to the generation of large chemical libraries of acetogenins.

  THF-环氧化合物8是由苄基（R）-（-）-缩水甘油基醚以10步合成方案以立体控制方式制备的。化合物8是用于合成单-和双-THF产乙酸素的高度有用的合成子。这种新的合成方法也可用于生成乙酸原素的大型化学文库。
• Synthesis of solamin type mono-THF acetogenins using cross-metathesis
  作者：Hiroyuki Konno、Hidefumi Makabe、Yasunao Hattori、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2010.08.028

  日期：2010.10

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.
• Convergent synthesis of (+)-muconin
  作者：Wen-Qian Yang、Takeshi Kitahara

  DOI：10.1016/s0040-4039(99)01629-9

  日期：1999.10

  An efficient total synthesis of the tetrahydropyran-bearing acetogenin muconin 1 is described. Palladium(0)-mediated crossed diyne coupling and the use of only D-glutamic acid as the origin of all absolute stereochemistry highlight this flexible approach thar sets the stage for access to structural analogs for further study. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Kuriyama, Wataru; Ishigami, Ken; Kitahara, Takeshi, Heterocycles, 1999, vol. 50, # 2, p. 981 - 988
  作者：Kuriyama, Wataru、Ishigami, Ken、Kitahara, Takeshi

  DOI：——

  日期：——