3-(2'-O-prop-1"-enyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)prop-1-ene | 252202-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2'-O-prop-1"-enyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)prop-1-ene
• 英文别名: (2R,3R,4R,5S,6S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-prop-2-enoxy-6-prop-2-enyloxane
• CAS: 252202-48-5
• 化学式: C₃₃H₃₈O₅
• 分子量: 514.662
• InChiKey: UIQNKVNSUISCQZ-RGPGAZMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2'-O-prop-1"-enyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)prop-1-ene 在 Grubbs catalyst first generation 、 氨 、 sodium 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 (1S,3R,6R,8S,9R,10R)-6-(4-methoxyphenyl)-2,5,7,11-tetraoxatricyclo[8.5.0.03,8]pentadec-13-en-9-ol
  参考文献：
  名称：

  Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C

  摘要：

  Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00041-8
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 3-(2'-O-prop-1"-enyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)prop-1-ene
  参考文献：
  名称：

  Synthesis and stereochemical confirmation of the cis-fused L/M and N/O ring systems of maitotoxin

  摘要：

  Stereocontrolled synthesis of cis-fused 1,6-dioxadecalin system 1, which corresponds to the L/M and N/O rings of maitotoxin, was accomplished. Comparison of its H-1 and C-13 NMR data with those of the natural toxin established the earlier stereochemical assignments.

  DOI：

  10.1016/s0040-4039(00)73310-7

文献信息

• Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C-CTX-1
  作者：Makoto Sasaki、Miku Seida、Atsushi Umehara

  DOI：10.1021/acs.joc.2c02414

  日期：2023.1.6

  Convergent and scalable synthesis of the ABCDE-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera poisoning in the Caribbean Sea and the Northeast Atlantic areas, is described in detail. The key features of the synthesis include an iterative use of 2,2,6,6-tetramethyl piperidine 1-oxyl (TEMPO)/PhI(OAc)2-mediated oxidative lactonization and Suzuki–Miyaura coupling

  详细描述了加勒比海和东北大西洋地区雪卡毒素中毒的主要致病毒素加勒比雪卡毒素 C-CTX-1 的 ABCDE 环片段的收敛和可扩展合成。合成的主要特征包括迭代使用 2,2,6,6-四甲基哌啶 1-氧基 (TEMPO)/PhI(OAc) 2介导的氧化内酯化和 Suzuki–Miyaura 偶联到 DE 环系统和收敛片段耦合，通过铃木-宫浦耦合策略形成 ABCDE 环骨架。
• A very short route to the functionalized A-ring moiety of ciguatoxin
  作者：Hiroki Oguri、Shin-ichiro Tanaka、Tohru Oishi、Masahiro Hirama

  DOI：10.1016/s0040-4039(99)02185-1

  日期：2000.2

  The functionalized AB-ring moiety of ciguatoxin has been synthesized in a highly convergent manner via transition metal catalysis. (C) 2000 Elsevier Science Ltd. Alt rights reserved.
• 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.
• A Short Synthesis of the A/B Ring Systems of the Pacific Ciguatoxins P-CTX-3C and Dihydroxy-P-CTX-3C
  作者：Ludvig Eriksson、Sharon Guy、Patrick Perlmutter、Richard Lewis

  DOI：10.1021/jo990389c

  日期：1999.10.1
• Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C
  作者：Megumi Maruyama、Masayuki Inoue、Tohru Oishi、Hiroki Oguri、Yoshihiro Ogasawara、Yumi Shindo、Masahiro Hirama

  DOI：10.1016/s0040-4020(02)00041-8

  日期：2002.3

  Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.