N^α-(9-phenylfluoren-9-yl)-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-γ,δ-dehydro-D-lysine methyl ester | 230973-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N^α-(9-phenylfluoren-9-yl)-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-γ,δ-dehydro-D-lysine methyl ester
• 英文别名: methyl (E,2R)-3,3-dimethyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(9-phenylfluoren-9-yl)amino]hex-4-enoate
• CAS: 230973-52-1
• 化学式: C₃₃H₃₈N₂O₄
• 分子量: 526.676
• InChiKey: YSJXVKAQQYABPG-BSKIJULFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-(9-phenylfluoren-9-yl)-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-γ,δ-dehydro-D-lysine methyl ester 在 palladium on activated charcoal N-甲基吗啉 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 34.0h， 生成 N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester
  参考文献：
  名称：

  Synthesis of β,β-Dimethylated Amino Acid Building Blocks Utilizing the 9-Phenylfluorenyl Protecting Group

  摘要：

  Optically pure beta,beta-dimethylated amino acid building blocks with functionalized side chains have been prepared from D-aspartic acid. The dimethylation was accomplished by regioselective dialkylation of 9-phenylfluorenyl (PhFl)-protected aspartate diesters. The bulk of the PhFl protecting group also allowed for a variety of functional group manipulations to be carried out on the side chain without, affecting the C-alpha ester of the aspartate. As a result, the derivatives of the following novel amino acids were synthesized in this study: beta,beta-dimethyl-D-aspartic acid, beta,beta-dimethyl-D-homoserine, 3,3-dimethyl-D-2,4-diaminobutyric acid, beta,beta-dimethyl-D-lysine, beta,beta-dimethyl-D-homoglutamate, beta,beta-dimethyl-D-ornithine, and 3,3-dimethylazetidine-2-carboxylic acid. The beta,beta-dimethylated amino acids were synthesized in high enantiomeric excess as determined by coupling the, novel building blocks to chiral reagents.

  DOI：

  10.1021/jo982474a
• 作为产物：
  描述：

  (2R)-3,3-dimethyl-4-oxo-2-<(9-phenylfluoren-9-yl)amino>butyric acid methyl ester 在 叠氮化锂 、 TEA 、 水 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 三苯基膦 作用下， 以 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 68.5h， 生成 N^α-(9-phenylfluoren-9-yl)-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-γ,δ-dehydro-D-lysine methyl ester
  参考文献：
  名称：

  Synthesis of β,β-Dimethylated Amino Acid Building Blocks Utilizing the 9-Phenylfluorenyl Protecting Group

  摘要：

  Optically pure beta,beta-dimethylated amino acid building blocks with functionalized side chains have been prepared from D-aspartic acid. The dimethylation was accomplished by regioselective dialkylation of 9-phenylfluorenyl (PhFl)-protected aspartate diesters. The bulk of the PhFl protecting group also allowed for a variety of functional group manipulations to be carried out on the side chain without, affecting the C-alpha ester of the aspartate. As a result, the derivatives of the following novel amino acids were synthesized in this study: beta,beta-dimethyl-D-aspartic acid, beta,beta-dimethyl-D-homoserine, 3,3-dimethyl-D-2,4-diaminobutyric acid, beta,beta-dimethyl-D-lysine, beta,beta-dimethyl-D-homoglutamate, beta,beta-dimethyl-D-ornithine, and 3,3-dimethylazetidine-2-carboxylic acid. The beta,beta-dimethylated amino acids were synthesized in high enantiomeric excess as determined by coupling the, novel building blocks to chiral reagents.

  DOI：

  10.1021/jo982474a

文献信息

• Synthesis of β,β-Dimethylated Amino Acid Building Blocks Utilizing the 9-Phenylfluorenyl Protecting Group
  作者：Noriyuki Kawahata、Michael Weisberg、Murray Goodman

  DOI：10.1021/jo982474a

  日期：1999.6.1

  Optically pure beta,beta-dimethylated amino acid building blocks with functionalized side chains have been prepared from D-aspartic acid. The dimethylation was accomplished by regioselective dialkylation of 9-phenylfluorenyl (PhFl)-protected aspartate diesters. The bulk of the PhFl protecting group also allowed for a variety of functional group manipulations to be carried out on the side chain without, affecting the C-alpha ester of the aspartate. As a result, the derivatives of the following novel amino acids were synthesized in this study: beta,beta-dimethyl-D-aspartic acid, beta,beta-dimethyl-D-homoserine, 3,3-dimethyl-D-2,4-diaminobutyric acid, beta,beta-dimethyl-D-lysine, beta,beta-dimethyl-D-homoglutamate, beta,beta-dimethyl-D-ornithine, and 3,3-dimethylazetidine-2-carboxylic acid. The beta,beta-dimethylated amino acids were synthesized in high enantiomeric excess as determined by coupling the, novel building blocks to chiral reagents.