(2E,4S,5S)-4,5-isopropylidenedioxy-6-tert-butyldiphenylsilyloxy-2-hexenic acid ethyl ester | 1221741-37-2

• 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: (2E,4S,5S)-4,5-isopropylidenedioxy-6-tert-butyldiphenylsilyloxy-2-hexenic acid ethyl ester
• 英文别名: ethyl (E)-3-[(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 1221741-37-2
• 化学式: C₂₇H₃₆O₅Si
• 分子量: 468.665
• InChiKey: XCHQTXDQLRHMLK-ZPVZNFAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,4S,5S)-4,5-isopropylidenedioxy-6-tert-butyldiphenylsilyloxy-2-hexenic acid ethyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(2E,4S,5S)-4,5-isopropylidenedioxy-6-tert-butyldiphenylsilyloxy-2-hexen-1-ol
  参考文献：
  名称：

  Toward the stereoselective synthesis of C1–C23 fragment of spirastrellolide B

  摘要：

  A convergent synthesis of the protected C(1)-C(23) fragment 4 of the targeted natural product spirast-rellolide B is described. The key step of the synthesis is cross metathesis (CM) and TBAF promoted oxa-Michael to construct tetrahydropyran moiety. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.111
• 作为产物：
  描述：

  4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 (2E,4S,5S)-4,5-isopropylidenedioxy-6-tert-butyldiphenylsilyloxy-2-hexenic acid ethyl ester
  参考文献：
  名称：

  Toward the stereoselective synthesis of C1–C23 fragment of spirastrellolide B

  摘要：

  A convergent synthesis of the protected C(1)-C(23) fragment 4 of the targeted natural product spirast-rellolide B is described. The key step of the synthesis is cross metathesis (CM) and TBAF promoted oxa-Michael to construct tetrahydropyran moiety. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.111

文献信息

• Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone
  作者：Feng-Feng Gan、Shao-Bo Yang、Yong-Chun Luo、Wan-Bang Yang、Peng-Fei Xu

  DOI：10.1021/jo100183d

  日期：2010.4.16

  A new, efficient synthesis of sphingofungin F has been accomplished with 10.4% overall yield in 15 steps. The salient features of the synthesis are the utilization of methyl tricyclic iminolactone 3 for the asymmetric aldol reaction as a key step to introduce two desired stereogenic centers, one-pot reaction for the synthesis of omega-hydroxyketone from epsilon-caprolactone, and an effective one-step deprotection strategy to remove all protecting groups using 0.2 N HCl.
• Toward the stereoselective synthesis of C1–C23 fragment of spirastrellolide B
  作者：Akkapalli Rajesh、Gangavaram V.M. Sharma、Krishna Damera

  DOI：10.1016/j.tetlet.2014.05.111

  日期：2014.7

  A convergent synthesis of the protected C(1)-C(23) fragment 4 of the targeted natural product spirast-rellolide B is described. The key step of the synthesis is cross metathesis (CM) and TBAF promoted oxa-Michael to construct tetrahydropyran moiety. (C) 2014 Elsevier Ltd. All rights reserved.