benzyl ((S)-1-(((1R,2R)-2-((S)-2-((R)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanamido)cyclohexyl)amino)-1-oxopropan-2-yl)carbamate | 1004788-10-6

• 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: benzyl ((S)-1-(((1R,2R)-2-((S)-2-((R)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanamido)cyclohexyl)amino)-1-oxopropan-2-yl)carbamate
• CAS: 1004788-10-6
• 化学式: C₃₄H₅₅N₅O₇
• 分子量: 645.84
• InChiKey: XBYWSYBSQDDHRO-HJUXKYQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  163.96
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl ((S)-1-(((1R,2R)-2-((S)-2-((R)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanamido)cyclohexyl)amino)-1-oxopropan-2-yl)carbamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成
  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
• 作为产物：
  描述：

  、 BOC-D-亮氨酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 以82 mg的产率得到benzyl ((S)-1-(((1R,2R)-2-((S)-2-((R)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanamido)cyclohexyl)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