(R)-4-benzyl-3-[(S)-(5-tert-butyldimethylsilanyloxy)-(S)-3-hydroxy-(R)-2-methyl-7-trimethylsilyl-hept-6-ynoyl]-oxazolidin-2-one | 1196718-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-4-benzyl-3-[(S)-(5-tert-butyldimethylsilanyloxy)-(S)-3-hydroxy-(R)-2-methyl-7-trimethylsilyl-hept-6-ynoyl]-oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2R,3S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-methyl-7-trimethylsilylhept-6-ynoyl]-1,3-oxazolidin-2-one
• CAS: 1196718-49-6
• 化学式: C₂₇H₄₃NO₅Si₂
• 分子量: 517.813
• InChiKey: GOZOOXXOZSULAD-BUZMGHMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-[(S)-(5-tert-butyldimethylsilanyloxy)-(S)-3-hydroxy-(R)-2-methyl-7-trimethylsilyl-hept-6-ynoyl]-oxazolidin-2-one 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(R)-4-benzyl-3-[(S)-3-(R)-5-bis-(tert-butyl-dimethylsilanyloxy)-(R)-2-methyl-7-trimethylsilyl-hept-6-ynoyl]-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of the C1–C12 fragment of the thuggacins

  摘要：

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.015
• 作为产物：
  描述：

  (3S)-5-trimethylsilyl-3-(tert-butyldimethylsilanyl-oxy)-4-pentynaldehyde 、 (R)-(-)-4-苄基-3-丙酰基-2-恶唑烷酮 在 n-Bu2BOTf 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以77%的产率得到(R)-4-benzyl-3-[(S)-(5-tert-butyldimethylsilanyloxy)-(S)-3-hydroxy-(R)-2-methyl-7-trimethylsilyl-hept-6-ynoyl]-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of the C1–C12 fragment of the thuggacins

  摘要：

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.015

文献信息

• Stereoselective synthesis of the C1–C12 fragment of the thuggacins
  作者：Shoubin Tang、Zhengshuang Xu、Tao Ye

  DOI：10.1016/j.tetasy.2009.08.015

  日期：2009.9

  A concise asymmetric synthesis of the C1-C12 fragment of the antibacterial natural product thuggacins has been achieved. The stereochemistry of this fragment was established efficiently via stereoselective reduction and Evans-aldol condensation. Hanztsch's method and a Horner-Wadsworth-Emmnons reaction were employed for thiazole formation and the construction of the E-alpha,beta-unsaturated double bond. (C) 2009 Elsevier Ltd. All rights reserved.