Bz(2-I)-Gly(tBu)-Gly(tBu)-Gly(tBu)-NH2 | 1299449-83-4

• 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: Bz(2-I)-Gly(tBu)-Gly(tBu)-Gly(tBu)-NH2
• 英文别名: N-[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]-2-iodobenzamide
• CAS: 1299449-83-4
• 化学式: C₂₅H₃₉IN₄O₄
• 分子量: 586.514
• InChiKey: GXVBCIQSTXXIIT-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘苯甲酸 、 Fmoc-L-叔亮氨酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 Bz(2-I)-Gly(tBu)-Gly(tBu)-Gly(tBu)-NH2
  参考文献：
  名称：

  A peptide bromoiodinane approach for asymmetric bromolactonization

  摘要：

  A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.056
• 作为试剂：
  描述：

  3-苯基丙酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 lithium hydroxide monohydrate 、 Bz(2-I)-Gly(tBu)-Gly(tBu)-Gly(tBu)-NH2 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 58.5h， 生成 (S)-5-(bromomethyl)-5-phenyldihydrofuran-2(3H)-one 、 (R)-5-(bromomethyl)-5-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  A peptide bromoiodinane approach for asymmetric bromolactonization

  摘要：

  A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.056

文献信息

• A peptide bromoiodinane approach for asymmetric bromolactonization
  作者：Daniel C. Whitehead、Matthew Fhaner、Babak Borhan

  DOI：10.1016/j.tetlet.2011.02.056

  日期：2011.5

  A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology. (C) 2011 Elsevier Ltd. All rights reserved.