tert-butyl N-[(2S)-3-[(4-bromophenyl)methoxy]-1-[[(2R)-1-[[(2S)-1-[[(1R,2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-3-[(4-bromophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-phenylmethoxypropanoyl]amino]-3-phenylmethoxypropanoyl]amino]cyclohexyl]amino]-1-oxo-3-phenylmethoxypropan-2-yl]amino]-1-oxo-3-phenylmethoxypropan-2-yl]amino]-1-oxopropan-2-yl]carbamate | 1004788-03-7

• 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: tert-butyl N-[(2S)-3-[(4-bromophenyl)methoxy]-1-[[(2R)-1-[[(2S)-1-[[(1R,2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-3-[(4-bromophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-phenylmethoxypropanoyl]amino]-3-phenylmethoxypropanoyl]amino]cyclohexyl]amino]-1-oxo-3-phenylmethoxypropan-2-yl]amino]-1-oxo-3-phenylmethoxypropan-2-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 1004788-03-7
• 化学式: C₇₆H₉₄Br₂N₈O₁₆
• 分子量: 1535.43
• InChiKey: VTIJISTUNUTQDT-RPKJPSCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  102
• 可旋转键数：
  42
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  307
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  O-(4-bromo)-benzyl-boc-L-serine 、 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 以76 mg的产率得到tert-butyl N-[(2S)-3-[(4-bromophenyl)methoxy]-1-[[(2R)-1-[[(2S)-1-[[(1R,2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-3-[(4-bromophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-phenylmethoxypropanoyl]amino]-3-phenylmethoxypropanoyl]amino]cyclohexyl]amino]-1-oxo-3-phenylmethoxypropan-2-yl]amino]-1-oxo-3-phenylmethoxypropan-2-yl]amino]-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Self-Assembly of Noncyclic Bis-d- and l-tripeptides into Higher Order Tubular Constructs:  Design, Synthesis, and X-ray Crystal Superstructure

  摘要：

  Trans (1R,2R)-diaminocyclohexane was used as a semirigid vicinal diamine to anchor two N-protected tripeptides consisting Of L-D-L amino acids as carboxy terminal amides. The bis-tripeptide consisting of L-Ser (OBn)-D-Ser (OBn)-L-Ser (O-p-bromobenzyl) Boc afforded X-ray quality crystals containing benzene and chloroform solvent molecules. Analysis of the solid-state structure revealed a highly H-bonded helical open-ended tubular superstructure. The tripeptide strands intertwine like a pair of self-embracing arms, held together by a gamma-turn and a 14-membered antiparallel H-bonded macroring spanning the first and third amino acid residues within each strand. Whereas the tripeptide from the R,R anchor gave beautiful crystals from benzene and chloroform, the analogous construct from the S,S-anchored diamine gave a gel. Related bis-tripeptides with different amino acids showed extensive intramolecular H-bonding based on NMR titration and dilution experiments.

  DOI：

  10.1021/jo701621c