(2R,3R,4S)-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl | 243849-48-1

• 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,3R,4S)-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl
• 英文别名: triethyl-[2-[(2R,3R,4S)-3-methyl-4-phenylmethoxy-6-phenylsulfanyloxan-2-yl]ethoxy]silane
• CAS: 243849-48-1
• 化学式: C₂₇H₄₀O₃SSi
• 分子量: 472.764
• InChiKey: LJKSMECHVKOZLX-NSGKLNLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (2R,3R,4S,6S)-6-benzenesulfonyl-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-tetrahydropyran 、 (2R,3R,4S,6R)-6-benzenesulfonyl-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-tetrahydropyran
  参考文献：
  名称：

  Synthesis of the C29–C37 segment of spongistatin 1

  摘要：

  Starting from racemic 2 alpha-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the spongistatin E segment has been prepared in nine steps (2.3 steps per stereogenic center) with umpolung of anomeric reactivity at C37. This 3,5-syn-diol sequence completes our methodology to all stereoisomers of 3,5,7-trihydroxy heptanoic ester building blocks functionalized for alpha-oxyanion chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00148-2
• 作为产物：
  描述：

  苯基硫三甲基硅烷 在 咪唑 、 四丁基碘化铵 、 二异丁基氢化铝 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.17h， 生成 (2R,3R,4S)-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl
  参考文献：
  名称：

  Synthesis of the C29–C37 segment of spongistatin 1

  摘要：

  Starting from racemic 2 alpha-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the spongistatin E segment has been prepared in nine steps (2.3 steps per stereogenic center) with umpolung of anomeric reactivity at C37. This 3,5-syn-diol sequence completes our methodology to all stereoisomers of 3,5,7-trihydroxy heptanoic ester building blocks functionalized for alpha-oxyanion chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00148-2

文献信息

• Synthesis of the C29–C37 segment of spongistatin 1
  作者：Ralf Dunkel、Jens Treu、H.Martin R Hoffmann

  DOI：10.1016/s0957-4166(99)00148-2

  日期：1999.4

  Starting from racemic 2 alpha-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the spongistatin E segment has been prepared in nine steps (2.3 steps per stereogenic center) with umpolung of anomeric reactivity at C37. This 3,5-syn-diol sequence completes our methodology to all stereoisomers of 3,5,7-trihydroxy heptanoic ester building blocks functionalized for alpha-oxyanion chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.