(2R,3S)-2-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-2-(undec-1-yn-1-yl)cyclopentan-1-one | 1059624-72-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3S)-2-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-2-(undec-1-yn-1-yl)cyclopentan-1-one
• 英文别名: (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-[tert-butyl(diphenyl)silyl]oxy-2-undec-1-ynylcyclopentan-1-one
• CAS: 1059624-72-4
• 化学式: C₃₈H₅₈O₃Si₂
• 分子量: 619.048
• InChiKey: NVRUBKNBQNPKCR-LFGICVIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-2-(undec-1-yn-1-yl)cyclopentan-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以95%的产率得到(2R,3S,Z)-2-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-2-(undec-1-en-1-yl)cyclopentan-1-one
  参考文献：
  名称：

  Highly selective approach for the total synthesis of (+)-heliconol A

  摘要：

  The total synthesis of heliconol A, a representative of a new class of polyketide-derived hemiketals containing a reduced furanocyclopentane unit, has been achieved via the stereoselective reduction of a ketone, the face selective dihydroxylation, a Sonogashira coupling reaction, and a cis-selective reduction as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.031
• 作为产物：
  描述：

  (2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-hydroxy-2-(undec-1-yn-1-yl)cyclopentan-1-one 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以72%的产率得到(2R,3S)-2-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-2-(undec-1-yn-1-yl)cyclopentan-1-one
  参考文献：
  名称：

  Highly selective approach for the total synthesis of (+)-heliconol A

  摘要：

  The total synthesis of heliconol A, a representative of a new class of polyketide-derived hemiketals containing a reduced furanocyclopentane unit, has been achieved via the stereoselective reduction of a ketone, the face selective dihydroxylation, a Sonogashira coupling reaction, and a cis-selective reduction as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.031

文献信息

• Highly selective approach for the total synthesis of (+)-heliconol A
  作者：Debendra K. Mohapatra、Bhaskar Chatterjee、Mukund K. Gurjar

  DOI：10.1016/j.tetasy.2008.05.031

  日期：2008.7

  The total synthesis of heliconol A, a representative of a new class of polyketide-derived hemiketals containing a reduced furanocyclopentane unit, has been achieved via the stereoselective reduction of a ketone, the face selective dihydroxylation, a Sonogashira coupling reaction, and a cis-selective reduction as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.