(1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-enyl methanesulfonate | 1009360-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-enyl methanesulfonate
• CAS: 1009360-14-8
• 化学式: C₄₃H₆₆O₉SSi₂
• 分子量: 815.229
• InChiKey: CHISKQVMZYTBDQ-HDEARUHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  55.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-enyl methanesulfonate 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以96%的产率得到(1S,5R,Z)-5-((2R,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-hydroxy-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)pent-3-enyl methanesulfonate
  参考文献：
  名称：

  Synthesis of the C(26)−C(42) and C(43)−C(67) Pyran-Containing Fragments of Amphidinol 3 via a Common Pyran Intermediate

  摘要：

  The pyran-containing fragments 1 and 2 of AM3 have been synthesized from the common pyran intermediate 3. Careful orchestration of the alcohol protecting groups was necessary to facilitate deprotection of alcohol functionality in the presence of the chemically sensitive polyene chain.

  DOI：

  10.1021/ol703042q
• 作为产物：
  描述：

  (1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-en-1-ol 、 甲基磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以90%的产率得到(1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-enyl methanesulfonate
  参考文献：
  名称：

  Synthesis of the C(26)−C(42) and C(43)−C(67) Pyran-Containing Fragments of Amphidinol 3 via a Common Pyran Intermediate

  摘要：

  The pyran-containing fragments 1 and 2 of AM3 have been synthesized from the common pyran intermediate 3. Careful orchestration of the alcohol protecting groups was necessary to facilitate deprotection of alcohol functionality in the presence of the chemically sensitive polyene chain.

  DOI：

  10.1021/ol703042q