tert-butyl-[(2S)-1-chloro-1-phenylsulfanylbut-3-en-2-yl]oxy-dimethylsilane | 776315-78-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl-[(2S)-1-chloro-1-phenylsulfanylbut-3-en-2-yl]oxy-dimethylsilane
• CAS: 776315-78-7
• 化学式: C₁₆H₂₅ClOSSi
• 分子量: 328.978
• InChiKey: KOFJNVLVVXSPBT-MLCCFXAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(2S)-1-chloro-1-phenylsulfanylbut-3-en-2-yl]oxy-dimethylsilane 在 2,6-二叔丁基-4-甲基吡啶 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 (1R,2S)-1-[[(1R,3R,6S,7R,9S,11R,13S,17R,19S,20R)-17-[(E,3S)-3,4-bis(naphthalen-2-ylmethoxy)but-1-enyl]-7-ethenyl-20-(naphthalen-2-ylmethoxy)-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-yl]oxy]-1-phenylsulfanylbut-3-en-2-ol
  参考文献：
  名称：

  Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin

  摘要：

  A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon.

  DOI：

  10.1021/ol0364475
• 作为产物：
  描述：

  (2S)-1-phenylthio-2-tert-butyldimethylsilyloxy-3-butene 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 生成 tert-butyl-[(2S)-1-chloro-1-phenylsulfanylbut-3-en-2-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Synthesis of trans-fused tetrahydrooxepins: stereoselective allylation of sulfur or fluoro-substituted tetrahydrooxepins

  摘要：

  An efficient route to the trans-fused tetrahydrooxepin corresponding to the E ring of ciguatoxin was developed. Wide screening of allylation reactions of sulfur or fluoro-substituted tetrahydrooxepin revealed that the optimum method for obtaining the beta-allylation product selectively was the use of a combination of allyltrimethylsilane and TiCl4 with 6-fluoro-7-hydroxytetrahydrooxepin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.018

文献信息

• Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C
  作者：Shoji Kobayashi、Yusuke Takahashi、Kazuo Komano、Babak H. Alizadeh、Yuuya Kawada、Tohru Oishi、Shin-ichiro Tanaka、Yoshihiro Ogasawara、Shin-ya Sasaki、Masahiro Hirama

  DOI：10.1016/j.tet.2004.07.010

  日期：2004.9

  The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin
  作者：Shoji Kobayashi、Babak H. Alizadeh、Shin-ya Sasaki、Hiroki Oguri、Masahiro Hirama

  DOI：10.1021/ol0364475

  日期：2004.3.1

  A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon.
• Synthesis of trans-fused tetrahydrooxepins: stereoselective allylation of sulfur or fluoro-substituted tetrahydrooxepins
  作者：Shoji Kobayashi、Makiko Hori、Masahiro Hirama

  DOI：10.1016/j.carres.2007.11.018

  日期：2008.2

  An efficient route to the trans-fused tetrahydrooxepin corresponding to the E ring of ciguatoxin was developed. Wide screening of allylation reactions of sulfur or fluoro-substituted tetrahydrooxepin revealed that the optimum method for obtaining the beta-allylation product selectively was the use of a combination of allyltrimethylsilane and TiCl4 with 6-fluoro-7-hydroxytetrahydrooxepin. (c) 2007 Elsevier Ltd. All rights reserved.