dimethyl (3S,4R)-4-(tert-butyldimethylsilyloxy)-3-methyl-2-oxo-6-trimethylsilylhex-5-ynyl-phosphonate | 1044739-31-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: dimethyl (3S,4R)-4-(tert-butyldimethylsilyloxy)-3-methyl-2-oxo-6-trimethylsilylhex-5-ynyl-phosphonate
• CAS: 1044739-31-2
• 化学式: C₁₈H₃₇O₅PSi₂
• 分子量: 420.634
• InChiKey: DXRVMTFMDFVOFJ-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylhex-5-enal 、 dimethyl (3S,4R)-4-(tert-butyldimethylsilyloxy)-3-methyl-2-oxo-6-trimethylsilylhex-5-ynyl-phosphonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以54%的产率得到(E)-(3R,4S,8S,9R,10S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,8,10-trimethyl-1-trimethylsilyldodeca-6,11-dien-1-yn-5-one
  参考文献：
  名称：

  Synthetic studies toward cytostatin, a natural product inhibitor of protein phosphatase 2A

  摘要：

  Synthetic approaches toward the natural product cytostatin, an inhibitor of protein phosphatase 2A possessing cytotoxic and antimetastatic activities, have been investigated. A formal synthesis of cytostatin has been achieved according to a strategy relying on the formation of the C8-C9 bond by a nucleophilic addition of a functionalized organolithium (C1-C8 subunit) to an aldehyde (C9-C13 subunit). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.012
• 作为产物：
  描述：

  ethyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-trimethylsilylpent-4-ynoate 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以72%的产率得到dimethyl (3S,4R)-4-(tert-butyldimethylsilyloxy)-3-methyl-2-oxo-6-trimethylsilylhex-5-ynyl-phosphonate
  参考文献：
  名称：

  Synthetic studies toward cytostatin, a natural product inhibitor of protein phosphatase 2A

  摘要：

  Synthetic approaches toward the natural product cytostatin, an inhibitor of protein phosphatase 2A possessing cytotoxic and antimetastatic activities, have been investigated. A formal synthesis of cytostatin has been achieved according to a strategy relying on the formation of the C8-C9 bond by a nucleophilic addition of a functionalized organolithium (C1-C8 subunit) to an aldehyde (C9-C13 subunit). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.012