α-benzylginkgolide B | 170288-58-1

• 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: α-benzylginkgolide B
• 英文别名: 10-O-benzyl ginkgolide B；10-O-benzyl-ginkgolide B；10-O-benzylginkgolide B；10-benzyl ginkgolide B
• CAS: 170288-58-1
• 化学式: C₂₇H₃₀O₁₀
• 分子量: 514.529
• InChiKey: PHJOWQWLQBFEEM-SFEQTYPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  137.82
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  α-benzylginkgolide B 在 甲醇 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.08h， 生成 (1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-butyl-5,12,17-trihydroxy-16-methyl-6-phenylmethoxy-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-15,18-dione
  参考文献：
  名称：

  Unique Reactivity of α-Alkoxy Ginkgolide Lactones to Nucleophilic Reagents: Preparation of New Lactol Derivatives

  摘要：

  已经发现，亲核试剂，即NaBH4、Grignard试剂和烷基锂，与银杏内酯和F-seco-银杏内酯中的α-烷氧基或酰氧基内酯部分独特地反应，生成内酯醇衍生物。反应迅速且停止在内酯醇阶段；Na、Mg和Li金属对构象刚性的笼状结构的强烈配位作用涉及反应的引发和终止阶段。F-seco-银杏内酯的NaBH4还原反应生成α-和β-内酯醇的平衡混合物，只有在经过对-苯基苯甲酸酰化后才能分离。得到的酰基内酯醇手性中心的阐明是通过NOE和利用具有空间位阻的7-羟基的CD/FDCD激子手性方法进行的。另一方面，银杏内酯B衍生物的烷基化反应在C-11内酯部分区域选择性和立体选择性地进行，这是由于Grignard和烷基锂试剂接近笼状银杏内酯分子的凸面。新的手性中心，即季碳内酯醇羟基，已通过NOE确定。这种简便的烷基化方案导致银杏内酯的深层次骨架转化，通过“烯烃/烯烃”和“烯烃/炔烃”环闭合复分解反应生成一类新的球形七环银杏内酯衍生物。

  DOI：

  10.1246/bcsj.78.1843
• 作为产物：
  描述：

  溴甲苯 、 ginkgolide B 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以326 mg的产率得到α-benzylginkgolide B
  参考文献：
  名称：

  Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts

  摘要：

  Ginkgolides A, B, C and J, together with bilobalide, are unique terpenoid components of the Ginkgo biloba tree. Due to similar chemical properties, their separation is quite tedious. We have developed an efficient and rapid protocol for separation of individual ginkgolides and bilobalide from G. biloba extracts. The procedure takes advantage of enhanced susceptibility of ginkgolides B and C to benzylation and the ease of separation of these products from ginkgolides A and J which do not react. The protocol is applicable to the previously reported enriched extracts prepared from G. biloba leaves. A single chromatographic step prior to benzylation provides bilobalide and mixture of ginkgolides A, B, C, and J. After benzylation, the individual ginkgolides are separated by chromatography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.08.026

文献信息

• Alkyl and alkoxycarbonyl derivatives of ginkgolide B
  作者：Lihong Hu、Zhongliang Chen、Yuyuan Xie、Yuanyin Jiang、Huawu Zhen

  DOI：10.1016/s0968-0896(00)00085-7

  日期：2000.6

  Alkyl and alkoxycarbonyl derivatives 6-24 of ginkgolide B, prepared in one step from ginkgolide B through alkylation and acylation and evaluated for their in vitro ability to inhibit the PAF-induced aggregation of rabbit platelets, show equivalent or superior activities to ginkgolide B. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Preparation of ginkgolide and F-seco-ginkgolide lactols: the unique reactivity of α-hydroxy lactones toward NaBH4
  作者：Katsunori Tanaka、Kimberly D. Kester、Nina Berova、Koji Nakanishi

  DOI：10.1016/j.tetlet.2004.10.113

  日期：2005.1

  It has been found that NaBH4 smoothly reduces the alpha-hydroxy-lactone moieties in ginkgolide and F-seco-ginkgolides to lactols. The reaction is rapid and stops at the lactol stage: the coordination of NNaBH4 to the conformationally rigid cage structure is involved in both the initiation and termination stages. This facile reduction of ginkgolide lactones yield a variety of new ginkgolide lactols. (C) 2004 Elsevier Ltd. All rights reserved.
• A Concise Synthesis of Ginkgolide M, a Minor Component of a Terpene Trilactone Fraction from <i>Ginkgo </i><i>b</i><i>iloba</i> Roots
  作者：Sergei Bolshakov、Sergei V. Dzyuba、John Decatur、Koji Nakanishi

  DOI：10.1021/np050403i

  日期：2006.3.1

  Ginkgolide M (GM), which is found only in the roots of the Ginkgo biloba tree and is an inhibitor of ligand-operated ion channels in the central nervous system, has been prepared in three steps from 10-benzylginkgolide C, an intermediate generated during the isolation and separation of ginkgolides from Ginkgo biloba leaf extract. The described synthetic sequence can be applied to access GM derivatives for biological studies.