N-(9H-fluoren-9-ylmethoxycarbonyl)-O-trityl-D-serine benzyl ester | 866832-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(9H-fluoren-9-ylmethoxycarbonyl)-O-trityl-D-serine benzyl ester
• CAS: 866832-84-0
• 化学式: C₄₄H₃₇NO₅
• 分子量: 659.781
• InChiKey: MOPRNJGDAVZOPS-VQJSHJPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.65
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(9H-fluoren-9-ylmethoxycarbonyl)-O-trityl-D-serine benzyl ester 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以85%的产率得到N-(9H-fluoren-9-ylmethoxycarbonyl)-D-serine benzyl ester
  参考文献：
  名称：

  Efficient Solid-Phase-Based Total Synthesis of the Bisintercalator TANDEM

  摘要：

  In this article, the first solid-phase-based total synthesis of TANDEM, a synthetic analogue of triostin A, is described. In initial studies, the synthesis incorporated depsipeptide formation, introduction of chromophores, and disulfide bond formation on the solid phase, prior to a final solution-phase macrolactamization, to give the target molecule. Although pure TANDEM was obtained in an overall yield comparable to those for all syntheses to date, the yield of the final cyclization was low (11%). A more efficient approach involved removal from the solid phase prior to disulfide bond formation. The resulting linear peptide underwent macrolactamization under mild conditions and high dilution. Final disulfide bond formation was essentially quantitative and gave the target molecule, TANDEM, in an overall yield of 18%. The final compound was assessed for its ability to bind to 5'-TpA sequences on DNA by DNase I footprinting. This efficient synthesis sets the stage for a study of the structure-activity relationship of TANDEM and the natural product triostin A, with analogues containing "point mutations" at every site within the cyclic compounds.

  DOI：

  10.1021/jo050959a
• 作为产物：
  描述：

  N-[芴甲氧羰基]-O-(三苯基甲基)-D-丝氨酸 、 溴甲苯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以89%的产率得到N-(9H-fluoren-9-ylmethoxycarbonyl)-O-trityl-D-serine benzyl ester
  参考文献：
  名称：

  Efficient Solid-Phase-Based Total Synthesis of the Bisintercalator TANDEM

  摘要：

  In this article, the first solid-phase-based total synthesis of TANDEM, a synthetic analogue of triostin A, is described. In initial studies, the synthesis incorporated depsipeptide formation, introduction of chromophores, and disulfide bond formation on the solid phase, prior to a final solution-phase macrolactamization, to give the target molecule. Although pure TANDEM was obtained in an overall yield comparable to those for all syntheses to date, the yield of the final cyclization was low (11%). A more efficient approach involved removal from the solid phase prior to disulfide bond formation. The resulting linear peptide underwent macrolactamization under mild conditions and high dilution. Final disulfide bond formation was essentially quantitative and gave the target molecule, TANDEM, in an overall yield of 18%. The final compound was assessed for its ability to bind to 5'-TpA sequences on DNA by DNase I footprinting. This efficient synthesis sets the stage for a study of the structure-activity relationship of TANDEM and the natural product triostin A, with analogues containing "point mutations" at every site within the cyclic compounds.

  DOI：

  10.1021/jo050959a