tert-butyl-[(1S)-2-[(2S,4S,5R,6S)-6-ethenyl-5-methyl-4-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxan-2-yl]-1-[(1R,2R)-2-methylcyclopropyl]ethoxy]-dimethylsilane | 1035662-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-[(1S)-2-[(2S,4S,5R,6S)-6-ethenyl-5-methyl-4-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxan-2-yl]-1-[(1R,2R)-2-methylcyclopropyl]ethoxy]-dimethylsilane
• CAS: 1035662-57-7
• 化学式: C₂₈H₅₂O₇Si
• 分子量: 528.802
• InChiKey: JVCRRCICBWBZNV-WSEPFBLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(1S)-2-[(2S,4S,5R,6S)-6-ethenyl-5-methyl-4-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxan-2-yl]-1-[(1R,2R)-2-methylcyclopropyl]ethoxy]-dimethylsilane 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以91%的产率得到2-[(2S,3S,4S,6S)-6-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(1R,2R)-2-methylcyclopropyl]ethyl]-3-methyl-4-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxan-2-yl]ethanol
  参考文献：
  名称：

  Total synthesis of clavosolide A

  摘要：

  For the total synthesis of (-)-clavosolide A described herein, a Schmidt glycosidation reaction was used to attach the sugar moiety at an early stage in the synthesis to the 4-hydroxy group of the substituted tetrahydropyran unit of the molecule, which itself was built following a Ti(III)-mediated method developed by us earlier, and at the end, it was the Yamaguchi reaction that was successfully employed for the cyclodimerization of the two halves of the molecule leading to its total synthesis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.039
• 作为产物：
  描述：

  、 甲基三苯基碘化膦 在 sodium amide 作用下， 以 乙醚 为溶剂， 反应 6.17h， 以67%的产率得到tert-butyl-[(1S)-2-[(2S,4S,5R,6S)-6-ethenyl-5-methyl-4-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxan-2-yl]-1-[(1R,2R)-2-methylcyclopropyl]ethoxy]-dimethylsilane
  参考文献：
  名称：

  Total synthesis of clavosolide A

  摘要：

  For the total synthesis of (-)-clavosolide A described herein, a Schmidt glycosidation reaction was used to attach the sugar moiety at an early stage in the synthesis to the 4-hydroxy group of the substituted tetrahydropyran unit of the molecule, which itself was built following a Ti(III)-mediated method developed by us earlier, and at the end, it was the Yamaguchi reaction that was successfully employed for the cyclodimerization of the two halves of the molecule leading to its total synthesis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.039

文献信息

• Total synthesis of clavosolide A
  作者：Tushar Kanti Chakraborty、Vakiti Ramkrishna Reddy、Praveen Kumar Gajula

  DOI：10.1016/j.tet.2008.03.039

  日期：2008.5

  For the total synthesis of (-)-clavosolide A described herein, a Schmidt glycosidation reaction was used to attach the sugar moiety at an early stage in the synthesis to the 4-hydroxy group of the substituted tetrahydropyran unit of the molecule, which itself was built following a Ti(III)-mediated method developed by us earlier, and at the end, it was the Yamaguchi reaction that was successfully employed for the cyclodimerization of the two halves of the molecule leading to its total synthesis. (c) 2008 Elsevier Ltd. All rights reserved.