(E,2S,4S,5R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-2-[(4-methoxyphenyl)methoxymethyl]-4,6,8-trimethyl-10-phenylmethoxydec-8-en-3-one | 753016-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E,2S,4S,5R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-2-[(4-methoxyphenyl)methoxymethyl]-4,6,8-trimethyl-10-phenylmethoxydec-8-en-3-one
• CAS: 753016-44-3
• 化学式: C₄₅H₅₈O₆Si
• 分子量: 723.037
• InChiKey: ZBTKCXHXRRJBMS-NIPBVZBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E,2S,4S,5R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-2-[(4-methoxyphenyl)methoxymethyl]-4,6,8-trimethyl-10-phenylmethoxydec-8-en-3-one 在 二乙基甲氧基硼烷 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.25h， 以73%的产率得到(E,2S,3S,4S,5R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-2-[(4-methoxyphenyl)methoxymethyl]-4,6,8-trimethyl-10-phenylmethoxydec-8-ene-3,5-diol
  参考文献：
  名称：

  First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination

  摘要：

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.

  DOI：

  10.1021/ol049219z
• 作为产物：
  描述：

  2-hydroxymethyl-1-(4-methoxybenzyloxy)-3-pentanone 在 咪唑 、 tin(II) trifluoromethanesulfonate 、 乙酸乙烯酯 、 lipase AK 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E,2S,4S,5R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-2-[(4-methoxyphenyl)methoxymethyl]-4,6,8-trimethyl-10-phenylmethoxydec-8-en-3-one
  参考文献：
  名称：

  A practical synthesis of (−)-kazusamycin A (revised)

  摘要：

  We describe herein a stereo-controlled and practical synthesis of three key building blocks, namely Segment AB', Segment D, and Segment E' needed for the total synthesis of (-)-kazusamycin A. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.029

文献信息

• First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination
  作者：Noriyoshi Arai、Noriko Chikaraishi、Satoshi Omura、Isao Kuwajima

  DOI：10.1021/ol049219z

  日期：2004.8.1

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.
• A practical synthesis of (−)-kazusamycin A (revised)
  作者：Shengfeng Zhou、Huaxiang Chen、Wensheng Liao、Shu-Hui Chen、Ge Li、Ryoichi Ando、Isao Kuwajima

  DOI：10.1016/j.tetlet.2005.07.029

  日期：2005.9

  We describe herein a stereo-controlled and practical synthesis of three key building blocks, namely Segment AB', Segment D, and Segment E' needed for the total synthesis of (-)-kazusamycin A. (c) 2005 Elsevier Ltd. All rights reserved.