benzyl (4S)-4-but-3-enyl-5-oxo-1,3-oxazolidine-3-carboxylate | 519156-50-4

• 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 (4S)-4-but-3-enyl-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 519156-50-4
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: DXPDSIHDTPNNIR-ZDUSSCGKSA-N

物化性质

• 沸点：
  445.9±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-4-but-3-enyl-5-oxo-1,3-oxazolidine-3-carboxylate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以64%的产率得到(S)-N-benzyloxycarbonyl-N-methyl-2-(3-butenyl)-glycine
  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 、 N-alpha-Cbz-L-赖氨酸 、 sodium acetate 在 sodium nitrite 、 camphor-10-sulfonic acid 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 2.0h， 以46%的产率得到benzyl (4S)-4-(4-acetyloxybutyl)-5-oxo-1,3-oxazolidine-3-carboxylate
  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

文献信息

• [EN] N-METHYL AMINO ACIDS<br/>[FR] ACIDES N-METHYL AMINES
  申请人：UBIQUITOUS TECHNOLOGIES PTY LT

  公开号：WO2004007427A1

  公开（公告）日：2004-01-22

  The present invention relates to a compound of formula (I) or (II), processes for preparing them, peptides including them and kits involving them.

  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。
• An Efficient Synthesis of <i>N</i>-Methyl Amino Acids by Way of Intermediate 5-Oxazolidinones
  作者：Luigi Aurelio、John S. Box、Robert T. C. Brownlee、Andrew B. Hughes、Marianne M. Sleebs

  DOI：10.1021/jo026722l

  日期：2003.4.1

  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.