(2S,3R,4R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylheptanal | 1242057-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylheptanal
• CAS: 1242057-51-7
• 化学式: C₂₄H₄₈O₄Si
• 分子量: 428.728
• InChiKey: UZKGHSZXYXAEOE-CBDMQDTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylheptanal 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 4.0h， 以89%的产率得到ethyl (E,4R,5R,6R,8R)-5-[tert-butyl(dimethyl)silyl]oxy-8-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-4,6-dimethylnon-2-enoate
  参考文献：
  名称：

  Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol

  摘要：

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.148
• 作为产物：
  描述：

  [(2R,3R)-3-[(2R,4R)-4-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]pentan-2-yl]-2-methyloxiran-2-yl]methanol 、 叔丁基二甲硅基三氟甲磺酸酯 在 N,N-二异丙基乙胺 作用下， 以76%的产率得到(2S,3R,4R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2,4-dimethylheptanal
  参考文献：
  名称：

  Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol

  摘要：

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.148

文献信息

• Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol
  作者：J.S. Yadav、Sk. Samad Hossain、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2010.05.148

  日期：2010.8

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.