N^α-benzyloxycarbonyl-p-(10B)borono-L-phenylalanine methyl ester | 1043926-52-8

• 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: N^α-benzyloxycarbonyl-p-(10B)borono-L-phenylalanine methyl ester
• CAS: 1043926-52-8
• 化学式: C₁₈H₂₀BNO₆
• 分子量: 356.36
• InChiKey: QZHFSZDNKNWGLG-FYHWDVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N^α-benzyloxycarbonyl-p-(10B)borono-L-phenylalanine methyl ester 在 盐酸 、 methyloxirane 作用下， 以 异丙醇 为溶剂， 反应 31.0h， 以83.1%的产率得到4-10硼酸-L-苯丙氨酸
  参考文献：
  名称：

  Development of the first and practical method for enantioselective synthesis of 10B-enriched p-borono-l-phenylalanine

  摘要：

  At present p-(B-10)borono-L-phenylalanine (L-(10)Bpa) is used clinically as an excellent B-10 carrier for BNCT; however, its enantioselective synthesis has not been reported yet. The present Letter describes the first and practical method for enantioselective synthesis of B-10-enriched L-Bpa using Z-L-Ser-OMe as the chiral synthon in good total yield and high optical purity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.108
• 作为产物：
  描述：

  N^α-benzyloxycarbonyl-p-[2,3-dihydro-1H-naphtho[1,8-de]-1,3-diaza-2-(10B)borinyl]-L-phenylalanine methyl ester 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94.6%的产率得到N^α-benzyloxycarbonyl-p-(10B)borono-L-phenylalanine methyl ester
  参考文献：
  名称：

  Development of the first and practical method for enantioselective synthesis of 10B-enriched p-borono-l-phenylalanine

  摘要：

  At present p-(B-10)borono-L-phenylalanine (L-(10)Bpa) is used clinically as an excellent B-10 carrier for BNCT; however, its enantioselective synthesis has not been reported yet. The present Letter describes the first and practical method for enantioselective synthesis of B-10-enriched L-Bpa using Z-L-Ser-OMe as the chiral synthon in good total yield and high optical purity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.108