[(2S)-1-[(2R,3S)-3-ethenyloxiran-2-yl]pentan-2-yl] (3S)-3-[(4-methoxyphenyl)methoxy]pent-4-enoate | 1263164-97-1

• 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)-1-[(2R,3S)-3-ethenyloxiran-2-yl]pentan-2-yl] (3S)-3-[(4-methoxyphenyl)methoxy]pent-4-enoate
• CAS: 1263164-97-1
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: YBIRTRDWXNEVPU-BVOGOJNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S)-1-[(2R,3S)-3-ethenyloxiran-2-yl]pentan-2-yl] (3S)-3-[(4-methoxyphenyl)methoxy]pent-4-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以78%的产率得到(1R,3S,7S,8Z,10S)-7-[(4-methoxyphenyl)methoxy]-3-propyl-4,11-dioxabicyclo[8.1.0]undec-8-en-5-one
  参考文献：
  名称：

  Total synthesis of Z-isomer of phomolide B

  摘要：

  We have achieved the synthesis of Z-isomer of phomolide B during our investigation toward the effect of protecting group on the outcome of ring-closing metathesis reaction. The other key reactions involved are cis-selective partial hydrogenation. Sharpless asymmetric epoxidation, Yamaguchi esteritication, and following 12 longest linear sequence with 18.5% overall yield starting from a known intermediate 20. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.003
• 作为产物：
  描述：

  (3S)-3-[(4-methoxybenzyl)oxy]pent-4-enoic acid 、 (2S)-1-[(2R,3S)-3-ethenyloxiran-2-yl]pentan-2-ol 在 2,4,6-三氯苯甲酰氯 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以92%的产率得到[(2S)-1-[(2R,3S)-3-ethenyloxiran-2-yl]pentan-2-yl] (3S)-3-[(4-methoxyphenyl)methoxy]pent-4-enoate
  参考文献：
  名称：

  Total synthesis of Z-isomer of phomolide B

  摘要：

  We have achieved the synthesis of Z-isomer of phomolide B during our investigation toward the effect of protecting group on the outcome of ring-closing metathesis reaction. The other key reactions involved are cis-selective partial hydrogenation. Sharpless asymmetric epoxidation, Yamaguchi esteritication, and following 12 longest linear sequence with 18.5% overall yield starting from a known intermediate 20. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.003

文献信息

• Total synthesis of Z-isomer of phomolide B
  作者：Debendra K. Mohapatra、D. Prabhakar Reddy、Uttam Dash、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.11.003

  日期：2011.1

  We have achieved the synthesis of Z-isomer of phomolide B during our investigation toward the effect of protecting group on the outcome of ring-closing metathesis reaction. The other key reactions involved are cis-selective partial hydrogenation. Sharpless asymmetric epoxidation, Yamaguchi esteritication, and following 12 longest linear sequence with 18.5% overall yield starting from a known intermediate 20. (C) 2010 Elsevier Ltd. All rights reserved.