(2R,3S)-2-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-pent-4-ene-1,3-diol | 776315-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-2-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-pent-4-ene-1,3-diol
• 英文别名: (2R,3S)-2-[[(1S,3R,5S,6R,8R,9R,10S)-6-ethenyl-9-phenylmethoxy-2,7,11-trioxatricyclo[8.5.0.03,8]pentadec-13-en-5-yl]oxy]pent-4-ene-1,3-diol
• CAS: 776315-73-2
• 化学式: C₂₆H₃₄O₇
• 分子量: 458.552
• InChiKey: NWVFHHZNAIRNGR-PLWQKMRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-pent-4-ene-1,3-diol 在 Grubbs catalyst first generation 2,6-二甲基吡啶 、 盐酸 、 正丁基锂 、 三氯化铝 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 (+)-10-camphorsulfonic acid 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 硝基甲烷 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 160.58h， 生成
  参考文献：
  名称：

  Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.07.010
• 作为产物：
  描述：

  (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-ol 在 三乙基硅烷 、 四丁基氟化铵 作用下， 以 乙腈 、 四氢呋喃 为溶剂， 反应 44.67h， 以58%的产率得到(2R,3S)-2-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-pent-4-ene-1,3-diol
  参考文献：
  名称：

  Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.07.010

文献信息

• Oishi; Tanaka; Ogasawara, Synlett, 2001, # SPEC. ISS, p. 952 - 954
  作者：Oishi、Tanaka、Ogasawara、Maeda、Oguri、Hirama

  DOI：——

  日期：——
• 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.