(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde | 179944-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde
• 英文别名: (2S,3R)-3-[(2R,3R)-5-methoxy-3-methyloxolan-2-yl]-2-phenylmethoxybutanal
• CAS: 179944-88-8
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: YQSZBRUPOYOHPA-RTGYZTBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde 在 palladium on activated charcoal 正丁基锂 、 四丁基氟化铵 、 氨 、 氢气 、 碳酸氢钠 、 calcium 、 N,N-二异丙基乙胺 、 异丙醇 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol
  参考文献：
  名称：

  Synthesis and actin-depolymerizing activity of mycalolide analogs

  摘要：

  Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), was stereoselectively synthesized and was found to have strong actin-depolymerizing activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.078
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester 在 咪唑 、 草酰氯 、 四丁基氟化铵 、 氨 、 sodium 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.72h， 生成 (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde
  参考文献：
  名称：

  Aplyronine A, a Potent Antitumor Substance of Marine Origin, Aplyronines B and C, and Artificial Analogues:  Total Synthesis and Structure−Cytotoxicity Relationships

  摘要：

  The enantioselective total synthesis of aplyronine A (1), a potent antitumor substance of marine origin, was achieved by a convergent-approach Three segments 4, 5, and 6, corresponding to the C5-C11, C21-C27, and C28-C34 portions of aplyronine A (1), were prepared using:the Evans aldol reaction and the Sharpless epoxidation as key steps. The coupling reaction of 4 with iodide 7 followed by julia olefination with sulfone 8 gave the C5-C20 segment 9, while the julia coupling reaction between segments 5 and 6 provided the C21-C34 segment 10. Julia olefination between segments 9 and 10 and the subsequent four-carbon homologation reaction led to seco acid 83, which was converted into aplyronine A (1) by Yamaguchi lactonization followed by the introduction of two amino acids. The use of the [(3,4-dimethoxybenzyl)oxy]methyl group as a protecting group for the hydroxyl at C29 was crucial for this synthesis. The enantioselective synthesis of two natural congeners, aplyronines B (2) acid C (3), was also carried out using the intermediates for the synthesis of 1, which determined the absolute stereostructures of 2 and 3 unambiguously. To study the structure-cytotoxicity relationships of aplyronines, artificial analogues of 1 were synthesized and their cytotoxicities were evaluated: the trimethylserine moiety, two hydroxyl groups, and the side-chain portion in 1 turned out to be important in the potent cytotoxicity shown by 1. Biological studies with aplyronine A (1) showed that 1 inhibited polymerization of G-actin to F-actin and depolymerized F-actin to G-actin.

  DOI：

  10.1021/jo9606113

文献信息

• Synthetic Studies on Aplyronine A, a Potent Antitumor Substance of Marine Origin: Stereocontrolled Synthesis of the C21–C34 Segment
  作者：Hideo Kigoshi、Makoto Ojika、Kiyotake Suenaga、Tsuyoshi Mutou、Junko Hirano、Akira Sakakura、Takeshi Ogawa、Masanori Nisiwaki、Kiyoyuki Yamada

  DOI：10.1016/0040-4039(94)88035-2

  日期：1994.2

  The C21–C34 segment 2 of aplyronine A (1), a potent antitumor substance of marine origin, was synthesized enantioselectively in 25 steps (17% overall yield) from imide 11.

  丙烯醛A（1）的C21–C34片段2是一种有效的海洋来源抗肿瘤物质，是由酰亚胺11以25个步骤（总收率17％）对映选择性合成的。
• The C29–C34 parts of antitumor macrolide aplyronine A serve as versatile actin-affinity tags
  作者：Didik Huswo Utomo、Akari Fujieda、Kentaro Tanaka、Momoko Takahashi、Kentaro Futaki、Kenta Tanabe、Hideo Kigoshi、Masaki Kita

  DOI：10.1039/d1cc04259a

  日期：——

  interactions (PPI) is a promising strategy. We developed structurally-simplified C29–C34 side-chain analogs of aplyronine A (ApA), an antitumor marine macrolide. Among them, the analog possessing the C23 acyloxy group, the C29 N,N-dimethyl-L-alanine ester and the C34 N-methyl enamide showed potent actin-depolymerizing activity. Binding kinetics, molecular docking, and affinity-purification experiments revealed

  受基于蛋白质 - 蛋白质相互作用（PPI）的天然产物启发的抗癌药物开发是一种有前途的策略。我们开发了结构简化的 Aplyronine A (ApA) 的 C29-C34 侧链类似物，这是一种抗肿瘤海洋大环内酯。其中，具有C23酰氧基的类似物、C29 N , N-二甲基-L-丙氨酸酯和C34 N-甲基烯酰胺显示出有效的肌动蛋白解聚活性。结合动力学、分子对接和亲和纯化实验表明，它们是多功能的肌动蛋白亲和标签，可加速与细胞骨架动力学相关的作用模式的研究和基于 PPI 的药物先导药物的开发。
• Synthesis and biological activity of mycalolide analogs
  作者：Kiyotake Suenaga、Tomoyuki Kimura、Takeshi Kuroda、Keita Matsui、Saori Miya、Satomi Kuribayashi、Akira Sakakura、Hideo Kigoshi

  DOI：10.1016/j.tet.2006.06.046

  日期：2006.8

  Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The analog 4 was found to have strong actin-depolymerizing activity. (c) 2006 Elsevier Ltd. All rights reserved.