(S)-((3S,6S,8S)-8-(benzyloxy)-3-methylundec-1-en-6-yl) 3-(4-(2 (benzyloxy)ethoxy)phenyl)-2-(N-methylpent-4-enamido)propanoate | 1569356-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-((3S,6S,8S)-8-(benzyloxy)-3-methylundec-1-en-6-yl) 3-(4-(2 (benzyloxy)ethoxy)phenyl)-2-(N-methylpent-4-enamido)propanoate
• 英文别名: [(3S,6S,8S)-3-methyl-8-phenylmethoxyundec-1-en-6-yl] (2S)-2-[methyl(pent-4-enoyl)amino]-3-[4-(2-phenylmethoxyethoxy)phenyl]propanoate
• CAS: 1569356-04-2
• 化学式: C₄₃H₅₇NO₆
• 分子量: 683.929
• InChiKey: MQGIBZLYAPDXKU-KVEPGXCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.91
• 重原子数：
  50.0
• 可旋转键数：
  25.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-((3S,6S,8S)-8-(benzyloxy)-3-methylundec-1-en-6-yl) 3-(4-(2 (benzyloxy)ethoxy)phenyl)-2-(N-methylpent-4-enamido)propanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 (3S,10R,13S)-3-(4-(2-hydroxyethoxy)benzyl)-13-((S)-2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione
  参考文献：
  名称：

  The stereoselective total synthesis of PF1163A

  摘要：

  A stereoselective total synthesis of 13-membered macrocycle PF1163A, an antifungal agent, has been accomplished for the first time starting from D-xylose. This approach involves a diastereoselective allylation of lactal ether,(3a) reductive ring opening of tetrahydrofuran ring,(3b) asymmetric methylation reaction, Yamaguchi esterification, and ring closing metathesis as key steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.031
• 作为产物：
  描述：

  Boc-L-酪氨酸甲酯 在 2,4,6-三氯苯甲酰氯 、 sodium hydride 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 42.5h， 生成 (S)-((3S,6S,8S)-8-(benzyloxy)-3-methylundec-1-en-6-yl) 3-(4-(2 (benzyloxy)ethoxy)phenyl)-2-(N-methylpent-4-enamido)propanoate
  参考文献：
  名称：

  The stereoselective total synthesis of PF1163A

  摘要：

  A stereoselective total synthesis of 13-membered macrocycle PF1163A, an antifungal agent, has been accomplished for the first time starting from D-xylose. This approach involves a diastereoselective allylation of lactal ether,(3a) reductive ring opening of tetrahydrofuran ring,(3b) asymmetric methylation reaction, Yamaguchi esterification, and ring closing metathesis as key steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.031

文献信息

• The stereoselective total synthesis of PF1163A
  作者：Harish Kumar、A. Srinivas Reddy、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2014.01.031

  日期：2014.2

  A stereoselective total synthesis of 13-membered macrocycle PF1163A, an antifungal agent, has been accomplished for the first time starting from D-xylose. This approach involves a diastereoselective allylation of lactal ether,(3a) reductive ring opening of tetrahydrofuran ring,(3b) asymmetric methylation reaction, Yamaguchi esterification, and ring closing metathesis as key steps. (C) 2014 Elsevier Ltd. All rights reserved.