(8E,10S,14R,16S)-10-hydroxy-16-methoxy-14-methyl-13-oxa-1,5-dithiaspiro[5.11]heptadec-8-en-12-one | 1528762-23-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (8E,10S,14R,16S)-10-hydroxy-16-methoxy-14-methyl-13-oxa-1,5-dithiaspiro[5.11]heptadec-8-en-12-one
• CAS: 1528762-23-3
• 化学式: C₁₆H₂₆O₄S₂
• 分子量: 346.512
• InChiKey: WTXQUWKPLUIHSR-VRZRJBKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (8E,10S,14R,16S)-10-hydroxy-16-methoxy-14-methyl-13-oxa-1,5-dithiaspiro[5.11]heptadec-8-en-12-one 在 碘 、 calcium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以92%的产率得到dendrodolide A
  参考文献：
  名称：

  The first stereoselective synthesis of dendrodolide A

  摘要：

  The first stereoselective total synthesis of natural product, dendrodolide A (1) is described from readily available (R)-propylene oxide and 3-buten-1-ol as starting materials. The synthesis was achieved in 10 steps with an overall yield of 19.1%. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification, and ring-closing metathesis (RCM). 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.044
• 作为产物：
  描述：

  (2S,4R)-1-(2-allyl-1,3-dithian-2-yl)-4-((tert-butyldimethylsilyl)oxy)pentan-2-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 37.0h， 生成 (8E,10S,14R,16S)-10-hydroxy-16-methoxy-14-methyl-13-oxa-1,5-dithiaspiro[5.11]heptadec-8-en-12-one
  参考文献：
  名称：

  The first stereoselective synthesis of dendrodolide A

  摘要：

  The first stereoselective total synthesis of natural product, dendrodolide A (1) is described from readily available (R)-propylene oxide and 3-buten-1-ol as starting materials. The synthesis was achieved in 10 steps with an overall yield of 19.1%. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification, and ring-closing metathesis (RCM). 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.044

文献信息

• The first stereoselective synthesis of dendrodolide A
  作者：A. Venkanna、B. Siva、B. Poornima、K. Suresh Babu、J. Madhusudana Rao

  DOI：10.1016/j.tetlet.2013.11.044

  日期：2014.1

  The first stereoselective total synthesis of natural product, dendrodolide A (1) is described from readily available (R)-propylene oxide and 3-buten-1-ol as starting materials. The synthesis was achieved in 10 steps with an overall yield of 19.1%. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification, and ring-closing metathesis (RCM). 2013 Elsevier Ltd. All rights reserved.