L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester | 257628-10-7

• 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: L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester
• 英文别名: benzyl (2S)-3-[4-(bromomethyl)phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 257628-10-7
• 化学式: C₂₅H₂₄BrNO₄
• 分子量: 482.374
• InChiKey: UMKFAPMWSJHTRH-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester 在 钯 六甲基磷酰三胺 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 L-4-((di-tert-butyl)phosphonomethyl)phenylalanine
  参考文献：
  名称：

  Preparation of l-Nα-Fmoc-4-[di-(tert-butyl)phosphonomethyl]phenylalanine from l-tyrosine

  摘要：

  The unnatural amino acid analogue, 4-(phosphonomethyl)phenylalanine (Pmp, 2), has proven to be a valuable tool for studying protein-tyrosine kinase dependent signal transduction, where it is most often incorporated into peptides or peptide mimetics as a phosphatase-stable phosphotyrosyl mimetic. Although Pmp has been prepared previously bearing a number of protection strategies, the N-alpha-Fmoc 4- [di-(tert-butyl)phosphonomethyl] phenylalanine form [(N alpha-Fmoc-L-Pmp('Bu-2)-OH, 3] is particularly attractive since it can be cleanly introduced into peptides using standard Fmoc protocols. Synthesis of 3 was first reported as its (D/L)-racemate, and subsequently as its L-3 enantiomer, with the latter synthesis having relied on induction of chirality using a camphor sultam auxiliary. Reported herein is an alternate enantioselective synthesis of L-3 in high ensantiomeric purity by procedures which derive the stereochemistry of the final product directly from the starting amino acid, without the need for chiral induction. A key feature of the route is the racemization-free nucleophilic substitution of lithium di-tert-butyl phosphite onto protected 4-bromomethylphenylalanine (17). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00385-7
• 作为产物：
  描述：

  苄氧羰基-L-酪氨酸苄酯三氟甲烷磺酸酯 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 乙醇 、 四溴化碳 、 PdCl₂(PPh)3 、 N-甲基吗啉氧化物 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 27.83h， 生成 L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester
  参考文献：
  名称：

  Preparation of l-Nα-Fmoc-4-[di-(tert-butyl)phosphonomethyl]phenylalanine from l-tyrosine

  摘要：

  The unnatural amino acid analogue, 4-(phosphonomethyl)phenylalanine (Pmp, 2), has proven to be a valuable tool for studying protein-tyrosine kinase dependent signal transduction, where it is most often incorporated into peptides or peptide mimetics as a phosphatase-stable phosphotyrosyl mimetic. Although Pmp has been prepared previously bearing a number of protection strategies, the N-alpha-Fmoc 4- [di-(tert-butyl)phosphonomethyl] phenylalanine form [(N alpha-Fmoc-L-Pmp('Bu-2)-OH, 3] is particularly attractive since it can be cleanly introduced into peptides using standard Fmoc protocols. Synthesis of 3 was first reported as its (D/L)-racemate, and subsequently as its L-3 enantiomer, with the latter synthesis having relied on induction of chirality using a camphor sultam auxiliary. Reported herein is an alternate enantioselective synthesis of L-3 in high ensantiomeric purity by procedures which derive the stereochemistry of the final product directly from the starting amino acid, without the need for chiral induction. A key feature of the route is the racemization-free nucleophilic substitution of lithium di-tert-butyl phosphite onto protected 4-bromomethylphenylalanine (17). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00385-7

文献信息

• Preparation of l-Nα-Fmoc-4-[di-(tert-butyl)phosphonomethyl]phenylalanine from l-tyrosine
  作者：Zhu-Jun Yao、Yang Gao、Terrence R Burke

  DOI：10.1016/s0957-4166(99)00385-7

  日期：1999.9

  The unnatural amino acid analogue, 4-(phosphonomethyl)phenylalanine (Pmp, 2), has proven to be a valuable tool for studying protein-tyrosine kinase dependent signal transduction, where it is most often incorporated into peptides or peptide mimetics as a phosphatase-stable phosphotyrosyl mimetic. Although Pmp has been prepared previously bearing a number of protection strategies, the N-alpha-Fmoc 4- [di-(tert-butyl)phosphonomethyl] phenylalanine form [(N alpha-Fmoc-L-Pmp('Bu-2)-OH, 3] is particularly attractive since it can be cleanly introduced into peptides using standard Fmoc protocols. Synthesis of 3 was first reported as its (D/L)-racemate, and subsequently as its L-3 enantiomer, with the latter synthesis having relied on induction of chirality using a camphor sultam auxiliary. Reported herein is an alternate enantioselective synthesis of L-3 in high ensantiomeric purity by procedures which derive the stereochemistry of the final product directly from the starting amino acid, without the need for chiral induction. A key feature of the route is the racemization-free nucleophilic substitution of lithium di-tert-butyl phosphite onto protected 4-bromomethylphenylalanine (17). (C) 1999 Elsevier Science Ltd. All rights reserved.