[(S)-3-Benzyloxy-3-(methoxy-methyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester | 371193-51-0

• 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-Benzyloxy-3-(methoxy-methyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S)-4-[methoxy(methyl)amino]-4-oxo-3-phenylmethoxybutyl]carbamate
• CAS: 371193-51-0
• 化学式: C₁₈H₂₈N₂O₅
• 分子量: 352.431
• InChiKey: VVILTWFYRXTNBF-HNNXBMFYSA-N

物化性质

• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(S)-3-Benzyloxy-3-(methoxy-methyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 ((S)-3-Benzyloxy-4-oxo-butyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Covalent capture purification of polypeptides after SPPS via a linker removable under very mild conditions

  摘要：

  The covalent purification of polypeptides possessing an N-terminal cysteine or threonine residue via formation of a thiazolidine or oxazolidine with an aldehyde-functionalized-resin has been successfully demonstrated. To extend the applicability of this approach to any possible N-terminal residue, a special linker derived from (S)-4-amino-2-hydroxy-butyric acid was incorporated into peptidyl-resin. This linker represents the connecting point between the capture unit (cysteine) useful for the isolation of the desired polypeptide and the desired N-terminus. The target polypeptide was recovered by periodate oxidation, which cleaved the covalent bond between the linker and the last residue of polypeptide under very mild conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02110-x
• 作为产物：
  描述：

  (2S)-4-叔丁氧羰基氨基-2-羟基丁酸 在 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 [(S)-3-Benzyloxy-3-(methoxy-methyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Covalent capture purification of polypeptides after SPPS via a linker removable under very mild conditions

  摘要：

  The covalent purification of polypeptides possessing an N-terminal cysteine or threonine residue via formation of a thiazolidine or oxazolidine with an aldehyde-functionalized-resin has been successfully demonstrated. To extend the applicability of this approach to any possible N-terminal residue, a special linker derived from (S)-4-amino-2-hydroxy-butyric acid was incorporated into peptidyl-resin. This linker represents the connecting point between the capture unit (cysteine) useful for the isolation of the desired polypeptide and the desired N-terminus. The target polypeptide was recovered by periodate oxidation, which cleaved the covalent bond between the linker and the last residue of polypeptide under very mild conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02110-x