2,3,4-tri-O-acetyl-6-O-benzylglucosyl bromide | 180072-37-1

• 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: 2,3,4-tri-O-acetyl-6-O-benzylglucosyl bromide
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-bromo-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 180072-37-1
• 化学式: C₁₉H₂₃BrO₈
• 分子量: 459.291
• InChiKey: ONOMUNYRTLTXRU-FQBWVUSXSA-N

物化性质

• 沸点：
  478.7±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-O-benzylglucosyl bromide 在 bis(cyclopentadienyl)-titanium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以95%的产率得到3,4-Di-O-acetyl-6-O-benzyl-D-glucal
  参考文献：
  名称：

  使用（C p2 TiCl）2可以很容易地从糖基溴化物制备各种取代的糖基

  摘要：

  通过与（C p2 TiCl）2反应，高产率地将被醚，缩醛或酯保护基不同取代的糖基卤化物转化为相应的糖基。糖基氯的反应性低于类似的溴化物。

  DOI：

  10.1016/0040-4039(96)00865-9
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-benzyl-D-glucopyanose 生成 2,3,4-tri-O-acetyl-6-O-benzylglucosyl bromide
  参考文献：
  名称：

  Rapid Preparation of Variously Protected Glycals Using Titanium(III)

  摘要：

  Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)(2). This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. P-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

  DOI：

  10.1021/jo982447k

文献信息

• Electrochemical formation of glycals in THF
  作者：J.D Parrish、R.Daniel Little

  DOI：10.1016/s0040-4039(01)01544-1

  日期：2001.10

  existing electrochemical approaches to these types of species and is amenable to scale up for large-scale production. In addition, this work is intended to provide a means of employing electrochemistry that can be duplicated in most organic chemistry laboratories using readily available glassware and equipment.

  提出了一种从糖基溴化物生产不饱和糖的新方法。这项工作简化了对这些类型物质的现有电化学方法，并可以扩大规模以进行大规模生产。此外，这项工作旨在提供一种使用电化学的方法，可以使用现成的玻璃器皿和设备在大多数有机化学实验室中复制这种方法。
• Design, synthesis and biological evaluation of novel glycosylated diphyllin derivatives as topoisomerase II inhibitors
  作者：Da-Kuo Shi、Wei Zhang、Ning Ding、Ming Li、Ying-Xia Li

  DOI：10.1016/j.ejmech.2011.11.011

  日期：2012.1

  Recently, a novel glycosylated diphyllin derivative 11 which exhibiting potent anticancer activity by targeting topoisomerase IIα was reported by our group. In order to provide more molecules for structure-activity relationship (SAR) studies, 12 new glycosylated diphyllin analogs have been designed, synthesized, and evaluated for their biological activities. The SAR analysis revealed that (i) the sugar

  最近，我们小组报道了一种新的糖基化二叶素衍生物11，它通过靶向拓扑异构酶 IIα 表现出有效的抗癌活性。为了为构效关系 (SAR) 研究提供更多分子，我们设计、合成了 12 种新的糖基化叶木素类似物，并对其生物活性进行了评估。SAR 分析表明 (i) diphyllin 上的糖部分对于抗癌活性是必不可少的；(ii) 糖上的赤道 C4'-OH 优于轴向的，并且 (iii) 糖的 C4' 和 C6' 处适当的环状亲脂基团可能会增强抗癌活性。
• Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4--induced hepatic injury in vitro
  作者：S Saito、S Nagase、M Kawase、Y Nagamura

  DOI：10.1016/0223-5234(96)89552-3

  日期：1996.1

  Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively beta-D-glucuronopyranosyl-(1-->3)-beta-D-glucopyranose, -(1-->6)-alpha-D-glucopyranose, -(1-->6)-beta-D-glucopyranose, -(1-->6)-beta-D-galactopyranose, and beta-D-galacturonopyranosyl-(-->2)-beta-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl beta-D-glucuronopyranosyl-(1-->4)-alpha-D-glucopyranosyl-D-glycyrrhetinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and beta-D-glucuronopyranosyl-(1-->2)-beta-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with beta-D-glucuronopyranosyl-glucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal beta-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal beta-D-glucuronopyranose of 2 was replaced by beta-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.
• LUBINEAU, ANDRE;QUENEAU, YVES, TETRAHEDRON, 45,(1989) N1, C. 6697-6712
  作者：LUBINEAU, ANDRE、QUENEAU, YVES

  DOI：——

  日期：——