2,3,4,6-Tetra-O-benzoyl-α-L-glucopyranosyl bromide | 161442-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-Tetra-O-benzoyl-α-L-glucopyranosyl bromide
• CAS: 161442-11-1
• 化学式: C₃₄H₂₇BrO₉
• 分子量: 659.487
• InChiKey: WISFGQOOKBVKPD-FVYAUOJASA-N

物化性质

• 沸点：
  729.9±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 12-hydroxyjasmonate 、 2,3,4,6-Tetra-O-benzoyl-α-L-glucopyranosyl bromide 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 以100%的产率得到
  参考文献：
  名称：

  Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity

  摘要：

  "

  d-葡萄糖苷结构对茉莉酸葡萄糖苷的生物活性和靶标亲和力的重要性。

  "

  DOI：

  10.1039/c4ob02106a
• 作为产物：
  描述：

  1,2,3,4,6-Penta-O-benzoyl-L-glucopyranoside 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 2,3,4,6-Tetra-O-benzoyl-α-L-glucopyranosyl bromide
  参考文献：
  名称：

  Tetra-O-benzoylglucosylation: A New 1H Nuclear Magnetic Resonance Method for Determination of the Absolute Configuration of Secondary Alcohols

  摘要：

  A new method for determination of the absolute configuration of secondary alcohols based on the anisotropic effect and glycosylation-induced H-1 NMR shifts is described. The tetra-O-benzoyl-beta-glucosylation of secondary alcohols induces dramatic shifts in the aglycon H-1 NMR peaks. The differences between the proton chemical shifts of the D-glucosylated derivative and the free alcohol (Delta delta = delta(D) - delta(ROH)) or more significantly between their chemical shifts in the D- and L-glucosylated derivatives (Delta delta = delta(D) - delta(L)) are characteristic of the absolute configuration of the secondary chiral alcohol. Furthermore, in most cases the sign of the chemical shift difference of the carbinyl protons correlates with the absolute configuration of their carbons, namely positive or negative Delta delta are obtained for (R)- or (S)-carbinyl carbons, respectively. Moreover, this method involves the use of one enantiomer and generally a single derivatization is sufficient.

  DOI：

  10.1021/jo00101a023
• 作为试剂：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 2,3,4,6-Tetra-O-benzoyl-α-L-glucopyranosyl bromide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以5%的产率得到octa-O-benzyl α,β-trehalose
  参考文献：
  名称：

  Roennow, Tor E. C. L.; Meldel, Morten; Bock, Klaus, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 2, p. 197 - 212

  摘要：

  DOI：

文献信息

• Synthesis and Bioactivity of Potassium β-<scp>D</scp>-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds
  作者：Yoko NAKAMURA、Ryoji MIYATAKE、Sho INOMATA、Minoru UEDA

  DOI：10.1271/bbb.80338

  日期：2008.11.23

  Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. β-d-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (−)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.

  Albizzia SAman是一种豆科植物，它在白天气息张开的叶子，夜间则将叶子折叠休息。β-d-葡萄糖吡喃苷12-羟基茉莉酸酯（1）被鉴定为控制这种叶子运动的内源性化学因子。我们开发了一种简洁的合成方法，通过9个步骤从（+）-2合成光学上纯净的（−）-1，总产率为58%。同样，作为结构-活性关系（SAR）研究的类物质1的类似物，如epi-LCF（13）、对映体（14）和半乳糖苷（19）也被合成。SAR研究的结果强烈表明，1的闭叶活性的机制与甲基茉莉酸酯的机制不同，并且还表明涉及了一种不同类型的靶蛋白，该蛋白识别茉莉酸衍生物的反式异构体。