methyl (6S,7R,10S,11R,14S,15R,18S,19R)-7,11,15,19-tetrakis((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-4,8,12,16-tetraoxo-6,10,14,18-tetraphenyl-3-oxa-5,9,13,17-tetraazaicosan-20-oate | 323580-16-1

• 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: methyl (6S,7R,10S,11R,14S,15R,18S,19R)-7,11,15,19-tetrakis((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-4,8,12,16-tetraoxo-6,10,14,18-tetraphenyl-3-oxa-5,9,13,17-tetraazaicosan-20-oate
• CAS: 323580-16-1
• 化学式: C₆₆H₁₀₄N₄O₁₁Si₄
• 分子量: 1241.91
• InChiKey: FCINXPFWRDEXPP-SQZSLCRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.56
• 重原子数：
  85.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  188.85
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  甲酸 、 methyl (6S,7R,10S,11R,14S,15R,18S,19R)-7,11,15,19-tetrakis((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-4,8,12,16-tetraoxo-6,10,14,18-tetraphenyl-3-oxa-5,9,13,17-tetraazaicosan-20-oate 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到
  参考文献：
  名称：

  Phenylisoserine: A Versatile Amino Acid for the Construction of Novel β-Peptide Structures

  摘要：

  The N-Boc O-tert-butyldimethysilyi-substituted hexa-beta -peptide methyl ester 18 was constructed from the O-TBS ether of (-)-(2R, 3S)-phenylisoserine. By NMR, it was determined that this home beta -peptide adopts a highly stable beta -strand-type secondary structure in chloroform solution, which is stabilized by both hydrophobic interactions involving the OTBS methyl groups of residues i and i + 2, and inter-(five-membered)/intra (six-membered)-residue H-bonding interactions. These interactions are systematically repeated along the peptide chain and, thereby, operate in concert to stabilize the observed conformation of 18.

  DOI：

  10.1021/ja002700+
• 作为产物：
  描述：

  (2R,3S)-N-叔丁氧羰基-3-苯基异丝氨酸甲酯 在 N-甲基吗啉 、 咪唑 、 potassium trimethylsilonate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 methyl (6S,7R,10S,11R,14S,15R,18S,19R)-7,11,15,19-tetrakis((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-4,8,12,16-tetraoxo-6,10,14,18-tetraphenyl-3-oxa-5,9,13,17-tetraazaicosan-20-oate
  参考文献：
  名称：

  Phenylisoserine: A Versatile Amino Acid for the Construction of Novel β-Peptide Structures

  摘要：

  The N-Boc O-tert-butyldimethysilyi-substituted hexa-beta -peptide methyl ester 18 was constructed from the O-TBS ether of (-)-(2R, 3S)-phenylisoserine. By NMR, it was determined that this home beta -peptide adopts a highly stable beta -strand-type secondary structure in chloroform solution, which is stabilized by both hydrophobic interactions involving the OTBS methyl groups of residues i and i + 2, and inter-(five-membered)/intra (six-membered)-residue H-bonding interactions. These interactions are systematically repeated along the peptide chain and, thereby, operate in concert to stabilize the observed conformation of 18.

  DOI：

  10.1021/ja002700+