(2R,5R,1'R,1"R)-2-[1'-hydroxy-2'-propenyl]-5-[1"-hydroxytridecyl]-tetrahydrofuran | 1073740-59-6

• 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: (2R,5R,1'R,1"R)-2-[1'-hydroxy-2'-propenyl]-5-[1"-hydroxytridecyl]-tetrahydrofuran
• 英文别名: (2R,5R,1'R,1''R)-2-(1'-hydroxy-2'-propenyl)-5-(1''-hydroxytridecyl)tetrahydrofuran；(1R)-1-[(2R,5R)-5-[(1R)-1-hydroxyprop-2-enyl]oxolan-2-yl]tridecan-1-ol
• CAS: 1073740-59-6
• 化学式: C₂₀H₃₈O₃
• 分子量: 326.52
• InChiKey: UISVOIFVCRPDOY-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R,1'R,1"R)-2-[1'-hydroxy-2'-propenyl]-5-[1"-hydroxytridecyl]-tetrahydrofuran 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成
  参考文献：
  名称：

  THF-acetogenin 4-deoxyannomontacin 碳水化合物类似物的合成及其对人前列腺癌细胞系的细胞毒性

  摘要：

  含有 acetogenin 4-deoxyannonmontacin (4-DAN) 的 THF 因其对多种人类肿瘤细胞系的有效细胞毒性和相对简单的结构而引起了人们的兴趣。本文描述了4-DAN及其类似物的C-10差向异构体的合成和细胞毒性，所述类似物包含分别取代THF和丁烯内酯部分的碳水化合物和噻吩。关键的合成策略是通过烯烃交叉复分解将THF和丁烯内酯片段或其替代物结合起来。不同的类似物对人前列腺癌细胞系 LNCaP 和 PC3 表现出低微摩尔至纳摩尔范围的细胞毒性。发现一种相对简单的甘露糖连接的噻吩类似物的活性与 4-DAN 相似。

  DOI：

  10.1016/j.carres.2022.108671
• 作为产物：
  描述：

  (2R,5R,1'R,1''R)-2-(1'-hydroxy-2'-propenyl)-5-(1''-methoxymethoxy-tridecyl)tetrahydrofuran 在 盐酸 、 甲醇 、 水 作用下， 反应 24.0h， 以85%的产率得到(2R,5R,1'R,1"R)-2-[1'-hydroxy-2'-propenyl]-5-[1"-hydroxytridecyl]-tetrahydrofuran
  参考文献：
  名称：

  Synthesis of solamin type mono-THF acetogenins using cross-metathesis

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.08.028

文献信息

• Synthesis and antitumor activity of C-9 epimers of the tetrahydrofuran containing acetogenin 4-deoxyannoreticuin
  作者：Feng Wang、Akira Kawamura、David R. Mootoo

  DOI：10.1016/j.bmc.2008.08.030

  日期：2008.9

  the C-9 alcohol of 4-deoxyannoreticuin, in an attempt to assign the configuration at this position in the naturally occurring material. Unfortunately, identification of one or the other epimeric structures with the natural product was not possible because of the closeness of the physical data for all three compounds. Both C-9 epimeric analogues showed similar cytotoxicity in the low micromolar range

  基于 THF 和丁烯内酯烯烃前体的交叉复分解，开发了一种高度收敛的含有 acetogenins 的单四氢呋喃 (THF) 合成。这种方法被应用于 4-脱氧降糖素的 C-9 醇的差向异构体，试图在天然存在的材料中指定这个位置的构型。不幸的是，由于所有三种化合物的物理数据非常接近，因此无法用天然产物鉴定一种或另一种差向异构结构。两种 C-9 差向异构类似物在低微摩尔范围内对两种人类肿瘤细胞系 PC-3（前列腺）和 Jurkat（T 细胞白血病）显示出相似的细胞毒性。这一结果与之前对密切相关的 THF 醋酸素的研究形成对比，
• 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.
• Synthesis of carbohydrate analogues of the THF-acetogenin 4-deoxyannomontacin and their cytotoxicity against human prostate cancer cell lines
  作者：Patricia Gonzalez Periche、Amanda Ramdular、Naga V.S.D.K. Bhupathiraju、Teja Kalidindi、Delissa S. Johnson、Nagavarakishore Pillarsetty、David R. Mootoo

  DOI：10.1016/j.carres.2022.108671

  日期：2022.11

  attracted interest for its potent cytotoxicity against a broad range of human tumor cell lines, and relatively simple structure. Herein is described the synthesis and cytotoxicity of C-10 epimers of 4-DAN and analogues thereof comprising carbohydrate and thiophene substitutes for the THF and butenolide moieties respectively. The key synthetic ploy was the union of THF and butenolide segments or their substitutes

  含有 acetogenin 4-deoxyannonmontacin (4-DAN) 的 THF 因其对多种人类肿瘤细胞系的有效细胞毒性和相对简单的结构而引起了人们的兴趣。本文描述了4-DAN及其类似物的C-10差向异构体的合成和细胞毒性，所述类似物包含分别取代THF和丁烯内酯部分的碳水化合物和噻吩。关键的合成策略是通过烯烃交叉复分解将THF和丁烯内酯片段或其替代物结合起来。不同的类似物对人前列腺癌细胞系 LNCaP 和 PC3 表现出低微摩尔至纳摩尔范围的细胞毒性。发现一种相对简单的甘露糖连接的噻吩类似物的活性与 4-DAN 相似。