[(2R,3S)-1-[(4S,5S)-2,2-dimethyl-5-[(2S)-1-phenylmethoxypropan-2-yl]-1,3-dioxolan-4-yl]-3-methoxyhex-5-en-2-yl] 4-methylbenzenesulfonate | 1373885-45-0

• 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: [(2R,3S)-1-[(4S,5S)-2,2-dimethyl-5-[(2S)-1-phenylmethoxypropan-2-yl]-1,3-dioxolan-4-yl]-3-methoxyhex-5-en-2-yl] 4-methylbenzenesulfonate
• CAS: 1373885-45-0
• 化学式: C₂₉H₄₀O₇S
• 分子量: 532.698
• InChiKey: VDKGZPUSMOMOKU-NNKCCBOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-1-[(4S,5S)-2,2-dimethyl-5-[(2S)-1-phenylmethoxypropan-2-yl]-1,3-dioxolan-4-yl]-3-methoxyhex-5-en-2-yl] 4-methylbenzenesulfonate 在 甲醇 、 potassium carbonate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (2S,3S,5S)-5-[(1S)-1-methoxybut-3-enyl]-3-(methoxymethoxy)-2-[(2S)-1-phenylmethoxypropan-2-yl]oxolane
  参考文献：
  名称：

  Synthesis of the C38–C54 spiroketal segment of halichondrin B

  摘要：

  Stereoselective synthesis of the C38-C54 segment of a marine metabolite halichondrin B comprising KLM and N rings with a C44 spiroketal including 10 chiral centers is described. The salient features of the synthesis are Carreira's addition, Sharpless asymmetric dihydroxylation and double alkylation of TosMIC strategy and double vinyl coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.090
• 作为产物：
  描述：

  (2R,3S)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4S,5S)-2,2-dimethyl-5-[(2S)-1-phenylmethoxypropan-2-yl]-1,3-dioxolan-4-yl]hex-5-en-3-ol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 186.0h， 生成 [(2R,3S)-1-[(4S,5S)-2,2-dimethyl-5-[(2S)-1-phenylmethoxypropan-2-yl]-1,3-dioxolan-4-yl]-3-methoxyhex-5-en-2-yl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis of the C38–C54 spiroketal segment of halichondrin B

  摘要：

  Stereoselective synthesis of the C38-C54 segment of a marine metabolite halichondrin B comprising KLM and N rings with a C44 spiroketal including 10 chiral centers is described. The salient features of the synthesis are Carreira's addition, Sharpless asymmetric dihydroxylation and double alkylation of TosMIC strategy and double vinyl coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.090

文献信息

• Synthesis of the C38–C54 spiroketal segment of halichondrin B
  作者：J.S. Yadav、C. Nagendra Reddy、G. Sabitha

  DOI：10.1016/j.tetlet.2012.02.090

  日期：2012.5

  Stereoselective synthesis of the C38-C54 segment of a marine metabolite halichondrin B comprising KLM and N rings with a C44 spiroketal including 10 chiral centers is described. The salient features of the synthesis are Carreira's addition, Sharpless asymmetric dihydroxylation and double alkylation of TosMIC strategy and double vinyl coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.