(S)-2-Benzyloxy-4-tert-butoxycarbonylamino-butyric acid | 371193-49-6

• 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)-2-Benzyloxy-4-tert-butoxycarbonylamino-butyric acid
• 英文别名: (2S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylmethoxybutanoic acid
• CAS: 371193-49-6
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: DNVCYMSPJZCFCO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxy-4-tert-butoxycarbonylamino-butyric acid 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 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：

  二碳酸二叔丁酯 在 sodium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (S)-2-Benzyloxy-4-tert-butoxycarbonylamino-butyric acid
  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

文献信息

• COMPOUNDS
  申请人：New Pharma Licence Holdings Limited

  公开号：EP3224273A1

  公开（公告）日：2017-10-04
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：NEW PHARMA LICENCE HOLDINGS LTD

  公开号：WO2016083531A1

  公开（公告）日：2016-06-02

  The present invention provides a compound of formula (I), and its use in methods of treatment, including the treatment of bacterial infections. Methods for the preparation of the compound of formula (I) are also provided. The compound of formula (I) has the structure shown below, where -R6 and -R7 are each together with the carbonyl group and nitrogen alpha to the carbon to which it is attached an amino acid residue, except that R6 together with the carbonyl group and nitrogen alpha to the carbon to which it is attached is not a phenylalanine, leucine or valine residue and/or -R7 together with the carbonyl group and nitrogen alpha to the carbon to which it is attached is not a leucine, iso-leucine, phenylalanine, threonine, valine or nor-valine residue, and -T, -A1, -A2, -A3 and -R10 are as discussed in the application: