methyl (2S)-1-[2-[(2S,3R,6S)-6-[(2S,4E)-3-hydroxynona-4,8-dien-2-yl]-3-methyl-2-trimethylsilyloxyoxan-2-yl]-2-oxoacetyl]piperidine-2-carboxylate | 906067-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-1-[2-[(2S,3R,6S)-6-[(2S,4E)-3-hydroxynona-4,8-dien-2-yl]-3-methyl-2-trimethylsilyloxyoxan-2-yl]-2-oxoacetyl]piperidine-2-carboxylate
• CAS: 906067-20-7
• 化学式: C₂₇H₄₅NO₇Si
• 分子量: 523.742
• InChiKey: NFPXAFMNHMORFM-VNUZQZCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-[2-[(2S,3R,6S)-6-[(2S,4E)-3-hydroxynona-4,8-dien-2-yl]-3-methyl-2-trimethylsilyloxyoxan-2-yl]-2-oxoacetyl]piperidine-2-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(S)-1-{2-[(2S,3R,6S)-3-Methyl-6-((E)-(R)-1-methyl-2-oxo-octa-3,7-dienyl)-2-trimethylsilanyloxy-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Studies directed towards the synthesis of antascomicin A: stereoselective synthesis of the C1–C21 fragment of the molecule

  摘要：

  A stereoselective synthesis of the C1-C21 fragment of the non-immuno suppressive immunophilin-binding natural product, antascomicin A was achieved using, as key steps, highly stereoselective Aldol reactions to build the C1-C17 fragment and a Nozaki-Hiyama-Kishi reaction to couple it with the remaining C18-C21 moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.113
• 作为产物：
  描述：

  (E)-1-iodo-6-<(tert-butyldimethylsilyl)oxy>-1-hexene 在 chromium dichloride 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 三乙胺 、 二异丙胺 、 间氯过氧苯甲酸 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 25.5h， 生成 methyl (2S)-1-[2-[(2S,3R,6S)-6-[(2S,4E)-3-hydroxynona-4,8-dien-2-yl]-3-methyl-2-trimethylsilyloxyoxan-2-yl]-2-oxoacetyl]piperidine-2-carboxylate
  参考文献：
  名称：

  Studies directed towards the synthesis of antascomicin A: stereoselective synthesis of the C1–C21 fragment of the molecule

  摘要：

  A stereoselective synthesis of the C1-C21 fragment of the non-immuno suppressive immunophilin-binding natural product, antascomicin A was achieved using, as key steps, highly stereoselective Aldol reactions to build the C1-C17 fragment and a Nozaki-Hiyama-Kishi reaction to couple it with the remaining C18-C21 moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.113

文献信息

• Studies directed towards the synthesis of antascomicin A: stereoselective synthesis of the C1–C21 fragment of the molecule
  作者：Tushar Kanti Chakraborty、Bajjuri Krishna Mohan

  DOI：10.1016/j.tetlet.2006.05.113

  日期：2006.7

  A stereoselective synthesis of the C1-C21 fragment of the non-immuno suppressive immunophilin-binding natural product, antascomicin A was achieved using, as key steps, highly stereoselective Aldol reactions to build the C1-C17 fragment and a Nozaki-Hiyama-Kishi reaction to couple it with the remaining C18-C21 moiety. (c) 2006 Elsevier Ltd. All rights reserved.