(S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one | 115481-99-7

• 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: (S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one
• 英文别名: (2S)-N-(benzyloxycarbonyl)methionine methylidene ester；benzyl (4S)-4-(2-methylsulfanylethyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 115481-99-7
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: YVPSDJMDHVQMTC-LBPRGKRZSA-N

物化性质

• 沸点：
  489.9±40.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以90%的产率得到L-蛋氨酸
  参考文献：
  名称：

  Facile and rapid regeneration of free amino acids from N -benzyloxycarbonyl-5-oxazolidinones and from N -benzyloxycarbonylamino derivatives by treatment with BCl 3 in dichloromethane

  摘要：

  Reaction of benzyloxycarbonyl-5-oxazolidinones and of N-benzyloxycarbonylamino acids with BCl3 in dichloromethane at room temperature affords the corresponding free amino acids. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.011
• 作为产物：
  描述：

  聚合甲醛 、 CBZ-L-蛋氨酸甲酯 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以90%的产率得到(S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one
  参考文献：
  名称：

  甲醇碳酸氢钠水溶液通过5-恶唑烷酮温和再生氨基酸烷基酯的羧基

  摘要：

  一种简单的无消旋方法使得可以通过中间体5-恶唑烷酮再生氨基酸烷基酯的羧酸基团，该中间体通过在甲醇水溶液中用碳酸氢钠处理而水解。

  DOI：

  10.1016/j.tetlet.2003.08.028

文献信息

• A Simple and Rapid Protocol for<i>N</i>-Methyl-<i>α</i>-Amino Acids
  作者：G. Vidyasagar Reddy、D.S. Iyengar

  DOI：10.1246/cl.1999.299

  日期：1999.4

  A two step strategy for optically pure N-Protected-N-methyl-α-amino acids starting from N-protected-α-amino acids via reductive cleavage of oxazolidinones using NaCNBH3/TMSCl is described.

  描述了一种两步策略，从N-保护的α-氨基酸出发，通过使用NaCNBH3/TMSCl对恶唑烷酮进行还原性裂解，制备光学纯的N-保护-N-甲基-α-氨基酸。
• The Facile Production of N-Methyl Amino Acids via Oxazolidinones
  作者：Luigi Aurelio、Robert T. C. Brownlee、Andrew B. Hughes、Brad E. Sleebs

  DOI：10.1071/ch99082

  日期：——

  A range of oxazolidinones derived from N-carbamoylα-amino acids were prepared by an efficient method as key intermediatesin the synthesis of N-methyl amino acids and peptides.The method was readily applied to most α-amino acids except those withbasic side chains. The oxazolidinones were converted by reductive cleavageinto N-methyl α-amino acids.

  以N-氨基甲酰基α-氨基酸为原料，制备了一系列恶唑烷酮类化合物，作为合成N-甲基氨基酸和多肽的关键中间体。该方法适用于除碱性侧链以外的大多数α-氨基酸。恶唑烷酮通过还原裂解转化为N-甲基α-氨基酸。
• Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate
  作者：Pietro Allevi、Giuliana Cighetti、Mario Anastasia

  DOI：10.1016/s0040-4039(01)00971-6

  日期：2001.7

  The reaction of benzyloxycarbonyl-5-oxazolidinones with alcohols and sodium hydrogen carbonate to afford the corresponding benzyloxycarbonyl esters is described.

  描述了苄氧羰基-5-恶唑烷酮与醇和碳酸氢钠的反应，得到相应的苄氧羰基酯。
• 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.
• Asymmetric induction in nitrone cycloadditions: a total synthesis of acivicin by double asymmetric induction
  作者：Shadreck Mzengeza、Ralph Allen Whitney

  DOI：10.1021/jo00252a035

  日期：1988.8