methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate | 1138239-10-7

• 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 (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate
• 英文别名: (E)-methyl 4-{(4S,5R)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate；methyl (E)-4-[(4S,5R)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enoate
• CAS: 1138239-10-7
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: VOUKAKIXWXFYBO-HZAPPREKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到goniothalesdiol A
  参考文献：
  名称：

  First stereoselective total synthesis of Goniothalesdiol A

  摘要：

  The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.01.050
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 草酰氯 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 magnesium 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 22.0h， 生成 methyl (2E)-4-{(4S,5S)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}but-2-enoate
  参考文献：
  名称：

  A simple and efficient synthesis of goniothalesdiol A

  摘要：

  A concise, simple, and efficient stereoselective total synthesis of goniothalesdiol A starting from commercially available 2-deoxy-D-ribose is described herein using a stereocontrolled Grignard reaction, olefin cross-metathesis, and oxy-Michael addition reactions as the key steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.002

文献信息

• Stereoselective Total Synthesis of Goniothalesdiol A via Chiron Approach
  作者：Jhillu S. Yadav、Ragam Nageshwar Rao、Ragam Somaiah、Valaboju Harikrishna、Basi V. Subba Reddy

  DOI：10.1002/hlca.200900342

  日期：——

  The stereocontrolled synthesis of goniothalesdiol A, a dihydroxylated tetrahydropyran compound, has been accomplished using D‐ribose as chiral precursor. The key steps involved are aryl Grignard reaction, stereoselective alkoxy‐directed keto reduction, and intramolecular oxy‐Michael addition.

  使用D-核糖作为手性前体，可以完成立体式合成鼠李素A（一种二羟基化的四氢吡喃化合物）的立体控制。涉及的关键步骤是芳基格氏反应，立体选择性烷氧基指导的酮还原以及分子内氧迈克尔的加成。
• A simple and efficient synthesis of goniothalesdiol A
  作者：Pallavi Thakur、Kumaraswamy Boyapelly、Raji Reddy Gurram、Rakeshwar Bandichhor、Khagga Mukkanti

  DOI：10.1016/j.tetasy.2012.05.002

  日期：2012.5

  A concise, simple, and efficient stereoselective total synthesis of goniothalesdiol A starting from commercially available 2-deoxy-D-ribose is described herein using a stereocontrolled Grignard reaction, olefin cross-metathesis, and oxy-Michael addition reactions as the key steps. (C) 2012 Elsevier Ltd. All rights reserved.
• First stereoselective total synthesis of Goniothalesdiol A
  作者：J.S. Yadav、N. Rami Reddy、V. Harikrishna、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2009.01.050

  日期：2009.3

  The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre was fixed by intramolecular oxy-Michael addition. (C) 2009 Published by Elsevier Ltd.