(R)-5,6-dihydro-6-((E,3R,4S,5S,6S)-3-hydroxy-4,5,6-tris(methoxymethoxy)hept-1-enyl)pyran-2-one | 1256248-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (R)-5,6-dihydro-6-((E,3R,4S,5S,6S)-3-hydroxy-4,5,6-tris(methoxymethoxy)hept-1-enyl)pyran-2-one
• 英文别名: (2R)-2-[(E,3R,4S,5S,6S)-3-hydroxy-4,5,6-tris(methoxymethoxy)hept-1-enyl]-2,3-dihydropyran-6-one
• CAS: 1256248-92-6
• 化学式: C₁₈H₃₀O₉
• 分子量: 390.431
• InChiKey: NYWHUEVCDYLUFE-KCHGEQNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R)-5,6-dihydro-6-((E,3R,4S,5S,6S)-3-hydroxy-4,5,6-tris(methoxymethoxy)hept-1-enyl)pyran-2-one 在 盐酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 以80%的产率得到(2R)-2-[(E,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyhept-1-enyl]-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-anamarine via cross-metathesis protocol

  摘要：

  A convergent stereoselective total synthesis of (+)-anamarine via cross-metathesis (CM) protocol starting from 2-butyn-1,4-diol and vinyl lactone is reported. Other key features of the strategy include the use of Sharpless asymmetric epoxidation, Sharpless dihydroxylation, and Red-Al reduction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.077
• 作为产物：
  描述：

  (R)-6-vinyl-5,6-dihydro-2H-pyran-2-one 、 (3R,4S,5S,6S)-4,5,6-tris(methoxymethoxy)hept-1-en-3-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到(R)-5,6-dihydro-6-((E,3R,4S,5S,6S)-3-hydroxy-4,5,6-tris(methoxymethoxy)hept-1-enyl)pyran-2-one
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-anamarine via cross-metathesis protocol

  摘要：

  A convergent stereoselective total synthesis of (+)-anamarine via cross-metathesis (CM) protocol starting from 2-butyn-1,4-diol and vinyl lactone is reported. Other key features of the strategy include the use of Sharpless asymmetric epoxidation, Sharpless dihydroxylation, and Red-Al reduction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.077

文献信息

• Stereoselective total synthesis of (+)-anamarine via cross-metathesis protocol
  作者：Gowravaram Sabitha、C. Nagendra Reddy、Peddabuddi Gopal、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.08.077

  日期：2010.10

  A convergent stereoselective total synthesis of (+)-anamarine via cross-metathesis (CM) protocol starting from 2-butyn-1,4-diol and vinyl lactone is reported. Other key features of the strategy include the use of Sharpless asymmetric epoxidation, Sharpless dihydroxylation, and Red-Al reduction. (C) 2010 Elsevier Ltd. All rights reserved.