(+)-pinanediol 3-methylbutane-1-boronate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-pinanediol 3-methylbutane-1-boronate
• 英文别名: (1S,2S,6R,8S)-2,9,9-trimethyl-4-(3-methylbutyl)-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• 化学式: C₁₅H₂₇BO₂
• 分子量: 250.189
• InChiKey: IZFYOXHHLDCNCH-XPCVCDNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-pinanediol 3-methylbutane-1-boronate 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

  摘要：

  A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00682-0
• 作为产物：
  描述：

  magnesium,2-methylbutane,bromide 在 硫酸 作用下， 以 乙醚 为溶剂， 生成 (+)-pinanediol 3-methylbutane-1-boronate
  参考文献：
  名称：

  P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

  摘要：

  A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00682-0

文献信息

• A convergent approach to synthesis of bortezomib: the use of TBTU suppresses racemization in the fragment condensation
  作者：Andrey S. Ivanov、Anna A. Zhalnina、Sergey V. Shishkov

  DOI：10.1016/j.tet.2009.06.042

  日期：2009.8

  treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was found to efficiently suppress racemization in the fragment condensation. In comparison with the original synthesis, the presented one is shorter by two steps, higher in yield, and provides better atom economy.

  硼替佐米是一流的抗肿瘤治疗药物，用于治疗多发性骨髓瘤和套细胞淋巴瘤患者。在本文中，我们报告了一种使用收敛方法合成标题化合物的改进方法。发现TBTU可有效抑制碎片缩合中的外消旋作用。与原始合成方法相比，本文提出的方法缩短了两个步骤，产率更高，并且提供了更好的原子经济性。
• [EN] SYNTHESIS OF BORONIC ESTER AND ACID COMPOUNDS<br/>[FR] SYNTHESE D'ESTER BORIQUE ET DE COMPOSES ACIDES
  申请人：MILLENNIUM PHARM INC

  公开号：WO2005097809A3

  公开（公告）日：2006-02-16
• Tsai, David J. S.; Matteson, Donald S., Organometallics, 1983, vol. 2, # 2, p. 236 - 241
  作者：Tsai, David J. S.、Matteson, Donald S.

  DOI：——

  日期：——
• TSAL, D. J. S.;MATTESON, D. S., ORGANOMETALLICS, 1983, 2, N 2, 236-241
  作者：TSAL, D. J. S.、MATTESON, D. S.

  DOI：——

  日期：——
• P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease
  作者：E.Scott Priestley、Indawati De Lucca、Bahman Ghavimi、Susan Erickson-Viitanen、Carl P. Decicco

  DOI：10.1016/s0960-894x(02)00682-0

  日期：2002.11

  A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.