(3R)-3-triethylsilyloxyhexadecanoic acid | 334830-72-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R)-3-triethylsilyloxyhexadecanoic acid
• CAS: 334830-72-7
• 化学式: C₂₂H₄₆O₃Si
• 分子量: 386.691
• InChiKey: JZNZSRKBFFPRQE-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.55
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-benzotriazol-1-yl methanesulfonate 、 (3R)-3-triethylsilyloxyhexadecanoic acid 在 TEA 作用下， 以 四氢呋喃 为溶剂， 生成 benzotriazol-1-yl (3R)-3-triethylsilyloxyhexadecanoate
  参考文献：
  名称：

  The synthesis of pseudomycin C′ via a novel acid promoted side-chain deacylation of pseudomycin A

  摘要：

  The gamma hydroxyl present in the aliphatic side chain of the natural products pseudomycin A and C' provided a unique handle for the pH dependent side-chain deacylation. Low pH reaction conditions were used to cleave the side chain with minimal degradation of the peptide core. The pseudomycin nucleus intermediate obtained from the deacylation of pseudomycin A was pivotal in the synthesis of novel side-chain analogues. A practical synthesis of a minor fermentation factor pseudomycin C' and related analogues is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00613-2
• 作为产物：
  描述：

  3-氧代十六烷酸甲酯 在 咪唑 、 4-二甲氨基吡啶 、 Ru-(+)-BINAP 作用下， 以 二氯甲烷 为溶剂， 生成 (3R)-3-triethylsilyloxyhexadecanoic acid
  参考文献：
  名称：

  The synthesis of pseudomycin C′ via a novel acid promoted side-chain deacylation of pseudomycin A

  摘要：

  The gamma hydroxyl present in the aliphatic side chain of the natural products pseudomycin A and C' provided a unique handle for the pH dependent side-chain deacylation. Low pH reaction conditions were used to cleave the side chain with minimal degradation of the peptide core. The pseudomycin nucleus intermediate obtained from the deacylation of pseudomycin A was pivotal in the synthesis of novel side-chain analogues. A practical synthesis of a minor fermentation factor pseudomycin C' and related analogues is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00613-2

文献信息

• The synthesis of pseudomycin C′ via a novel acid promoted side-chain deacylation of pseudomycin A
  作者：Michael J Rodriguez、Matthew Belvo、Robert Morris、Douglas J Zeckner、William L Current、Roberta K Sachs、Mark J Zweifel

  DOI：10.1016/s0960-894x(00)00613-2

  日期：2001.1

  The gamma hydroxyl present in the aliphatic side chain of the natural products pseudomycin A and C' provided a unique handle for the pH dependent side-chain deacylation. Low pH reaction conditions were used to cleave the side chain with minimal degradation of the peptide core. The pseudomycin nucleus intermediate obtained from the deacylation of pseudomycin A was pivotal in the synthesis of novel side-chain analogues. A practical synthesis of a minor fermentation factor pseudomycin C' and related analogues is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.