(S)-2-tert-Butoxycarbonylamino-propionic acid 1-[2-(4-carboxymethyl-phenyl)-ethyl]-2-methyl-propyl ester | 220625-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-tert-Butoxycarbonylamino-propionic acid 1-[2-(4-carboxymethyl-phenyl)-ethyl]-2-methyl-propyl ester
• 英文别名: 2-[4-[4-methyl-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]oxypentyl]phenyl]acetic acid
• CAS: 220625-29-6
• 化学式: C₂₂H₃₃NO₆
• 分子量: 407.507
• InChiKey: OHESISFURLNZLZ-BUSXIPJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氨基-3-苄氧基羰基氨基丙酸 、 (S)-2-tert-Butoxycarbonylamino-propionic acid 1-[2-(4-carboxymethyl-phenyl)-ethyl]-2-methyl-propyl ester 生成 (S)-2-Amino-propionic acid 1-(2-{4-[(2-amino-1-carbamoyl-ethylcarbamoyl)-methyl]-phenyl}-ethyl)-2-methyl-propyl ester
  参考文献：
  名称：

  4-(3-Hydroxy-4-methylpentyl)phenylacetic acid as a new linker for the solid phase synthesis of peptides with Boc chemistry

  摘要：

  The anchoring the first amino acid in Boc chemistry to a 4-(3-hydroxy-4-methylpentyl)phenylacetic acid linker is described and compared to the conventional Pam resin. The peptidyl-4-(4-methyl-3-pentoxy)phenylacetamide linkage is slightly more stable to TFA than the Pam linker but in contrast to the Pam linker stable to cleavage of benzylic protective groups with TFMSA/DMS/TFA mixtures. This allows a mild and convenient two step deprotection procedure using the "low TFMSA-high HF". In HF this new linker reacts preferentially in an intramolecular reaction forming a tetrahydronaphthalene derivative. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02316-8
• 作为产物：
  描述：

  2-(4-Carboxymethyl-benzyl)-4-methyl-3-oxo-pentanoic acid ethyl ester 在 钯 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (S)-2-tert-Butoxycarbonylamino-propionic acid 1-[2-(4-carboxymethyl-phenyl)-ethyl]-2-methyl-propyl ester
  参考文献：
  名称：

  4-(3-Hydroxy-4-methylpentyl)phenylacetic acid as a new linker for the solid phase synthesis of peptides with Boc chemistry

  摘要：

  The anchoring the first amino acid in Boc chemistry to a 4-(3-hydroxy-4-methylpentyl)phenylacetic acid linker is described and compared to the conventional Pam resin. The peptidyl-4-(4-methyl-3-pentoxy)phenylacetamide linkage is slightly more stable to TFA than the Pam linker but in contrast to the Pam linker stable to cleavage of benzylic protective groups with TFMSA/DMS/TFA mixtures. This allows a mild and convenient two step deprotection procedure using the "low TFMSA-high HF". In HF this new linker reacts preferentially in an intramolecular reaction forming a tetrahydronaphthalene derivative. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02316-8