(3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate | 1117906-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate
• 英文别名: (-)-pericosine B；methyl (3R,4R,5R,6S)-3,4,5-trihydroxy-6-methoxycyclohexene-1-carboxylate
• CAS: 1117906-44-1
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: VUQJXZNNVAWIKZ-XUTVFYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3aS,4S,7R,7aR)-methyl 4-methoxy-7-(methoxymethoxy)-2,2-di-methyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 在 甲醇 、 三氟乙酸 作用下， 反应 24.0h， 生成 (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate
  参考文献：
  名称：

  Total synthesis of (+)-pericosine B and (+)-pericosine C and their enantiomers by using the Baylis–Hillman reaction and ring-closing metathesis as key steps

  摘要：

  A simple and divergent route for the total synthesis of pericosine B and pericosine C and their enantiomers from D-ribose by using the Baylis-Hillman reaction and ring-closing metathesis reactions as key steps has been described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.135

文献信息

• Synthesis of (−)-pericosine B, the antipode of the cytotoxic marine natural product
  作者：Yoshihide Usami、Kentaro Suzuki、Koji Mizuki、Hayato Ichikawa、Masao Arimoto

  DOI：10.1039/b813072h

  日期：——

  The stereoselective synthesis of (−)-pericosine B, which is the antipode of the cytotoxic metabolite of the fungus Periconia byssoides OUPS-N133 separated from the sea hare, was accomplished in 9 steps in 12% total yield from (−)-quinic acid, together with the synthesis of its epimer. Every crucial step of this total synthesis, including ring opening of a β-epoxide and NaBH4reduction of an unstable

  与海兔分离的真菌（Periconia byssoides OUPS-N133）的细胞毒性代谢产物的对映体（-）-pericosine B的立体选择性合成以9步完成，从（-）-奎宁酸的总收率为12％ ，连同其差向异构体的合成。整个合成过程中的每个关键步骤，包括β-环氧化物的开环和不稳定的β，γ-不饱和烯酮的NaBH 4还原，都具有出色的立体选择性。