(1S,2S,5S,6R)-3-aza-3-(fluoren-9-ylmethyloxycarbonyl)-6-[(tert-butyloxycarbonyl)aminomethyl]bicyclo[3.1.0]hexane-2-carboxylic acid | 1061736-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,5S,6R)-3-aza-3-(fluoren-9-ylmethyloxycarbonyl)-6-[(tert-butyloxycarbonyl)aminomethyl]bicyclo[3.1.0]hexane-2-carboxylic acid
• CAS: 1061736-86-4
• 化学式: C₂₇H₃₀N₂O₆
• 分子量: 478.545
• InChiKey: RIAYYYFYRLHGND-SCPDWHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,5S,6R)-3-aza-3-(fluoren-9-ylmethyloxycarbonyl)-6-[(tert-butyloxycarbonyl)aminomethyl]bicyclo[3.1.0]hexane-2-carboxylic acid 、 4-甲基三苯基氯甲烷 在 三氟乙酸 、 N,N-二异丙基乙胺 、 甲醇 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以65%的产率得到(1S,2S,5S,6R)-3-aza-3-(fluoren-9-ylmethyloxycarbonyl)-6-{[(4-methylphenyl)diphenylmethyl]aminomethyl}bicyclo[3.1.0]hexane-2-carboxylic acid
  参考文献：
  名称：

  Strategies for the Solid-Phase Diversification of Poly-l-proline-Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation

  摘要：

  A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pinc-N'-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH(2)Cl(2) followed by EDCI-mediated reaction of N-Pmc-N'-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.

  DOI：

  10.1021/jo8012258
• 作为产物：
  描述：

  (1S,2S,5S,6R)-3-aza-3-(fluoren-9-ylmethyloxycarbonyl)-6-[(tert-butyloxycarbonyl)aminomethyl]bicyclo[3.1.0]hexan-2-ylmethanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 phosphate buffer 、 水 、 乙腈 为溶剂， 以100%的产率得到(1S,2S,5S,6R)-3-aza-3-(fluoren-9-ylmethyloxycarbonyl)-6-[(tert-butyloxycarbonyl)aminomethyl]bicyclo[3.1.0]hexane-2-carboxylic acid
  参考文献：
  名称：

  Strategies for the Solid-Phase Diversification of Poly-l-proline-Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation

  摘要：

  A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pinc-N'-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH(2)Cl(2) followed by EDCI-mediated reaction of N-Pmc-N'-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.

  DOI：

  10.1021/jo8012258