(4S)-4-{4-[4-hydroxymethylimino-2-oxy-4H-(1,2,3,5)-oxatriazin-5-yl]-propyl}oxazolidin-5-one-3-carboxylic acid 9H-fluoren-9-ylmethyl ester | 519156-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4S)-4-{4-[4-hydroxymethylimino-2-oxy-4H-(1,2,3,5)-oxatriazin-5-yl]-propyl}oxazolidin-5-one-3-carboxylic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 4S-4-{4-[4-hydroxymethylimino-2-oxy-4H-(1,2,3,5)-oxatriazin-5-yl]-propyl}-oxazolidin-5-one-3-carboxylic acid 9H-fluoren-9-ylmethyl ester；9H-fluoren-9-ylmethyl (4S)-4-[3-[hydroxymethyl-(2-oxido-6H-1,2,3,5-oxatriazin-2-ium-4-yl)amino]propyl]-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 519156-56-0
• 化学式: C₂₄H₂₅N₅O₇
• 分子量: 495.492
• InChiKey: ZGPUXVXPEXABQB-NRFANRHFSA-N

物化性质

• 沸点：
  720.3±70.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S)-4-{4-[4-hydroxymethylimino-2-oxy-4H-(1,2,3,5)-oxatriazin-5-yl]-propyl}oxazolidin-5-one-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(2S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-5-[hydroxymethyl-(2-oxy-6H-[1,2,3,5]oxatriazin-4-yl)-amino]pentanoic acid
  参考文献：
  名称：

  [EN] N-METHYL AMINO ACIDS
  [FR] ACIDES N-METHYL AMINES

  摘要：

  这项发明涉及到式(I)或(II)的化合物，制备它们的方法，包括它们的肽和涉及它们的试剂盒。

  公开号：

  WO2004007427A1
• 作为产物：
  描述：

  聚合甲醛 、 Fmoc-Arg(NO2)-OH 在 camphor-10-sulfonic acid 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以67%的产率得到(4S)-4-{4-[4-hydroxymethylimino-2-oxy-4H-(1,2,3,5)-oxatriazin-5-yl]-propyl}oxazolidin-5-one-3-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  An Efficient Synthesis of N-Methyl Amino Acids by Way of Intermediate 5-Oxazolidinones

  摘要：

  N-Methyl amino acids occur in many natural products. Experimental strategies are presented for a unified approach to the synthesis of N-methyl derivatives through 5-oxazolidinones of the 20 common L-amino acids. The amino acids with reactive side chains that required protecting groups or devoted syntheses for side chain construction for N-methylation to proceed included serine, threonine, tyrosine, cysteine, methionine, tryptophan, asparagine, histidine, and arginine. The studies have provided improved methods for the preparation of N-methyl serine, threonine, and tyrosine. All 20 of the common L-amino acids are now available in suitable forms for solid or solution-phase peptide synthesis.

  DOI：

  10.1021/jo026722l