(1R)-1-(N-tert-butoxycarbonyl-L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid (+)-pinanediol ester | 1158975-00-8

• 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: (1R)-1-(N-tert-butoxycarbonyl-L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid (+)-pinanediol ester
• CAS: 1158975-00-8
• 化学式: C₃₅H₅₆BN₃O₇
• 分子量: 641.657
• InChiKey: VVRRVVLGFOPBKK-CMJXESQFSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  772.5±60.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  124.22
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R)-1-(N-tert-butoxycarbonyl-L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid (+)-pinanediol ester 、 三氟乙酸 以 氯仿 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of boronic acid derivatives of tyropeptin: Proteasome inhibitors

  摘要：

  Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.117
• 作为产物：
  描述：

  (aR,3aS,4S,6S,7aR)-六氢-3a,8,8-三甲基-alpha-(2-甲基丙基)-4,6-甲桥-1,3,2-苯并二氧硼烷-2-甲胺 2,2,2-三氟乙酸盐 、 Boc-Tyr(Me)-Val-OH 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以48%的产率得到(1R)-1-(N-tert-butoxycarbonyl-L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid (+)-pinanediol ester
  参考文献：
  名称：

  Synthesis of boronic acid derivatives of tyropeptin: Proteasome inhibitors

  摘要：

  Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.117