(1R,3R,6S,7R,9S,11R,13S,19S,20R)-7-(hydroxymethyl)-20-phenylmethoxy-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-ol | 676609-78-2

• 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: (1R,3R,6S,7R,9S,11R,13S,19S,20R)-7-(hydroxymethyl)-20-phenylmethoxy-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-ol
• CAS: 676609-78-2
• 化学式: C₂₄H₃₀O₇
• 分子量: 430.498
• InChiKey: RBEGAHCYYHCGKU-SIBYYXBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (1R,3R,6S,7R,9S,11R,13S,19S,20R)-7-(hydroxymethyl)-20-phenylmethoxy-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-ol 在 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 158.08h， 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：

  3-[4-benzyloxy-3-(4-methoxy-benzyloxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-(2-hydroxy-1-hydroxymethyl-but-3-enyloxy)-propan-1-one 在 Grubbs catalyst first generation 2,6-二甲基吡啶 、 三乙基硅烷 、 甲基锂 、 4-甲氧基苯甲醛 、 (+)-10-camphorsulfonic acid 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 52.92h， 生成 (1R,3R,6S,7R,9S,11R,13S,19S,20R)-7-(hydroxymethyl)-20-phenylmethoxy-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-ol
  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

• 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.
• 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.