(5R)-5-{[(tert-butyl)(diphenyl)silyl]oxy}hex-2-yn-1-ol | 1240372-11-5

• 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: (5R)-5-{[(tert-butyl)(diphenyl)silyl]oxy}hex-2-yn-1-ol
• 英文别名: (R)-5-(tert-butyldiphenylsilyloxy)hex-2-yn-1-ol；(5R)-5-[tert-butyl(diphenyl)silyl]oxyhex-2-yn-1-ol
• CAS: 1240372-11-5
• 化学式: C₂₂H₂₈O₂Si
• 分子量: 352.549
• InChiKey: DNBLKOCMDAIGMK-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R)-5-{[(tert-butyl)(diphenyl)silyl]oxy}hex-2-yn-1-ol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 AD-mix-α 、 甲基磺酰胺 、 对甲苯磺酸 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (2R,4S,5S)-6-((tert-butyldimethylsilyl)oxy)-4,5-dihydroxyhexan-2-yl acetate
  参考文献：
  名称：

  Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E

  摘要：

  A simple, first stereoselective total synthesis of botryolide-E has been described. The synthesis started from propylene oxide employing Jacobsen's hydrolytic kinetic resolution (HKR), selective epoxide opening, sharpless asymmetric dihydroxylation, one pot acetonide deprotection and lactonization as key steps. Further, the synthesis confirms the absolute configuration of the natural product botryolide-E and we evaluated the biological behavior of natural product botryolide-E against a panel of bacteria and fungi. Botryolide-E exhibits significant potent activity against Staphylococcus aureus (MTCC 96) (6.25 mu g/ml), good against Escherichia coli (MTCC 443) (12.5 mu g/ml), Bacillus subtilis (MTCC 441) (25 mu g/ml) and compound 1 exhibited good to moderate antifungal activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.024
• 作为产物：
  描述：

  (2R)-6-(tetrahydro-2H-pyran-2-yloxy)hex-4-yn-2-ol 在 咪唑 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (5R)-5-{[(tert-butyl)(diphenyl)silyl]oxy}hex-2-yn-1-ol
  参考文献：
  名称：

  Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E

  摘要：

  A simple, first stereoselective total synthesis of botryolide-E has been described. The synthesis started from propylene oxide employing Jacobsen's hydrolytic kinetic resolution (HKR), selective epoxide opening, sharpless asymmetric dihydroxylation, one pot acetonide deprotection and lactonization as key steps. Further, the synthesis confirms the absolute configuration of the natural product botryolide-E and we evaluated the biological behavior of natural product botryolide-E against a panel of bacteria and fungi. Botryolide-E exhibits significant potent activity against Staphylococcus aureus (MTCC 96) (6.25 mu g/ml), good against Escherichia coli (MTCC 443) (12.5 mu g/ml), Bacillus subtilis (MTCC 441) (25 mu g/ml) and compound 1 exhibited good to moderate antifungal activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.024

文献信息

• Stereoselective Total Synthesis of Ophiocerin C through Two Different Approaches
  作者：Malampati Srilatha、Biswanath Das

  DOI：10.1002/hlca.201400086

  日期：2014.11

  Stereoselective total synthesis of ophiocerin C has been accomplished through two different approaches starting separately from acetaldehyde and from (R)‐propylene oxide, and Sharpless asymmetric dihydroxylation has been employed as the key step in both approaches.

  ophiocerin C的立体选择性全合成是通过两种不同的方法完成的，分别从乙醛和（R）-环氧丙烷开始，并且Sharpless不对称二羟基化已被用作这两种方法中的关键步骤。
• A concise stereoselective total synthesis of Botryolide B
  作者：B. Chennakesava Reddy、H.M. Meshram

  DOI：10.1016/j.tetlet.2010.05.079

  日期：2010.8

  The first total synthesis of Botryolide B is described from easily accessible starting materials. The synthetic strategy involves Jacobsen resolution, Sharpless epoxidation, Swern oxidation, Yamaguchi reaction, and ring closing metathesis (RCM). (C) 2010 Elsevier Ltd. All rights reserved.