methyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-α-D-galactopyranoside | 78950-23-9

• 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: methyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-α-D-galactopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-p-bromobenzoyl-α-D-galactopyranoside；methyl 2,3,4,6-tetra-O-(p-bromobenzoyl)-α-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-tris[(4-bromobenzoyl)oxy]-6-methoxyoxan-2-yl]methyl 4-bromobenzoate
• CAS: 78950-23-9
• 化学式: C₃₅H₂₆Br₄O₁₀
• 分子量: 926.201
• InChiKey: JYESNPYPYZSTLC-UQPXDNIZSA-N

物化性质

• 沸点：
  857.0±65.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(2R,3S,4S,5R,6R)-3,4,5-tris[(4-bromobenzoyl)oxy]-6-methoxyoxan-2-yl]methyl 4-bromobenzoate 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到methyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Alkyl Galactopyranosides:  Rotational Population Dependence of the Hydroxymethyl Group on the Aglycon and Its Absolute Configuration and on the Anomeric Configuration

  摘要：

  The rotational populations of the hydroxymethyl group in chiral and nonchiral alkyl alpha- and beta-galactopyranosides proved, on the basis of circular dichroism (CD) and H-1 NMR data, to be dependent on the structure of the aglycon: the population of the gt and tg rotamers increased and decreased, respectively, as the pK(a) of the bonded alcohol (aglycon) increased, while the population of the gg rotamer remained practically constant. Furthermore, low-temperature CD measurements proved that the most stable rotamer is the gt, and not the tg. In addition, a clear correlation between the rotational populations and the absolute configuration of the chiral aglycon was observed; namely, higher and smaller gt and tg populations were observed for the (S)-alkyl beta-D-galactopyranosides than for their (R)-alkyl beta-D-galactopyranoside counterparts, the opposite behavior being observed for the cl-anomers. The results point to the exo anomeric effect as being responsible for these rotational dependencies, as well as to nonbonding interactions between the aglycon and the chromophore at C6 for those stereoisomers having in their aglycon a bulky substituent syn to the endocyclic oxygen (O5). In addition, the chemical shift differences (Delta delta) of the aglyconic protons of galactosylated chiral alcohols proved to be characteristic of the absolute configuration of the bonded chiral alcohol.

  DOI：

  10.1021/jo981002t

文献信息

• Characterization of methyl glycosides at the pico- to nano-gram level
  作者：Jerzy Golik、Hung-Wen Liu、Michael Dinovi、Jun Furukawa、Koji Nakanishi

  DOI：10.1016/0008-6215(83)88042-2

  日期：1983.7

  Abstract We describe a general method that permits characterization of 100-pg to 1-ng quantities of sugars. Thus, oligosaccharides are subjected to methanolysis, followed by per- p -bromobenzoylation or pernaphthoylation, and the methyl glycoside peresters are separated by high-pressure liquid chromatography. The method is also applicable to amino and acetamido sugars. If required, the separated sugar

  摘要我们描述了一种通用的方法，该方法可以表征100 pg至1 ng量的糖。因此，将寡糖进行甲醇分解，然后进行对-溴苯甲酰化或萘甲酰化，并通过高压液相色谱法分离甲基糖苷过酸酯。该方法也适用于氨基糖和乙酰氨基糖。如果需要，可以通过溴苯甲酸酯的特征准M +峰和激子分裂的圆二色性（cd）曲线的极值明确标识分离的糖衍生物。此外，由于聚苯甲酸酯的cd极值可从组分二苯甲酸酯单元的极值中预测出来，因此cd数据可得出有关吡喃葡萄糖的-OH，-NH 2和-NHAc基团未知空间分布的信息。该方法的应用已通过绿色戊糖C进行了证明，
• Ectyoplasides A–B – Unique Triterpene Oligoglycosides from the Caribbean SpongeEctyoplasia ferox
  作者：Francesco Cafieri、Ernesto Fattorusso、Orazio Taglialatela-Scafati

  DOI：10.1002/(sici)1099-0690(199901)1999:1<231::aid-ejoc231>3.0.co;2-u

  日期：1999.1

  Two novel norlanostane triglycosides, ectyoplasides A (1) and B (2), have been isolated from the methanolic extracts of the Caribbean sponge Ectyoplasiaferox (Raspaliidae, Axinellida). Their structures have been established by extensive application of high-resolution FABMS and two-dimensional NMR techniques, supported by chemical and enzymatic degradation methods. Ectyoplasides A and B have been shown

  从加勒比海绵 Ectyoplasiaferox（Raspaliidae，Axinellida）的甲醇提取物中分离出两种新型去甲羊毛脂烷三糖苷，ectyoplasides A (1) 和 B (2)。它们的结构是通过广泛应用高分辨率 FABMS 和二维核磁共振技术建立的，并得到化学和酶促降解方法的支持。Ectyoplasides A 和 B 已被证明具有相同的糖链（由两个 β-半乳糖单元和一个 α-阿拉伯糖单元组成），但它们的苷元部分不同，它们具有在环 A 上具有前所未有的取代模式的去甲三萜骨架。当对各种细胞系进行体外测试时，A 和 B 显示出中等的细胞毒活性
• Quinofuracins A–E, Produced by the Fungus <i>Staphylotrichum boninense</i> PF1444, Show p53-Dependent Growth Suppression
  作者：Daisuke Tatsuda、Isao Momose、Tetsuya Someno、Ryuichi Sawa、Yumiko Kubota、Masatomi Iijima、Takao Kunisada、Takumi Watanabe、Masakatsu Shibasaki、Akio Nomoto

  DOI：10.1021/np500581m

  日期：2015.2.27

  Quinofuracins A-E, novel anthraquinone derivatives containing beta-D-galactofuranose that were isolated from the fungus Staphylotrichum boninense PF1444, induced p53-dependent cell death in human tumor cells. The structures of quinofuracins A-E, including absolute configurations, were elucidated by extensive spectroscopic analysis and chemical transformation studies. Quinofuracins were classified into three groups according to the aglycone moieties. 5'-Oxoaverantin was present in quinofuracins A-C, whereas averantin and versicolorin B were identified in quinofuracins D and E, respectively. These quinofuracins induced p53-dependent growth suppression in human glioblastoma LNZTA3 cells.
• Alkyl Galactopyranosides:  Rotational Population Dependence of the Hydroxymethyl Group on the Aglycon and Its Absolute Configuration and on the Anomeric Configuration
  作者：Juan I. Padrón、Ezequiel Q. Morales、Jesús T. Vázquez

  DOI：10.1021/jo981002t

  日期：1998.11.1

  The rotational populations of the hydroxymethyl group in chiral and nonchiral alkyl alpha- and beta-galactopyranosides proved, on the basis of circular dichroism (CD) and H-1 NMR data, to be dependent on the structure of the aglycon: the population of the gt and tg rotamers increased and decreased, respectively, as the pK(a) of the bonded alcohol (aglycon) increased, while the population of the gg rotamer remained practically constant. Furthermore, low-temperature CD measurements proved that the most stable rotamer is the gt, and not the tg. In addition, a clear correlation between the rotational populations and the absolute configuration of the chiral aglycon was observed; namely, higher and smaller gt and tg populations were observed for the (S)-alkyl beta-D-galactopyranosides than for their (R)-alkyl beta-D-galactopyranoside counterparts, the opposite behavior being observed for the cl-anomers. The results point to the exo anomeric effect as being responsible for these rotational dependencies, as well as to nonbonding interactions between the aglycon and the chromophore at C6 for those stereoisomers having in their aglycon a bulky substituent syn to the endocyclic oxygen (O5). In addition, the chemical shift differences (Delta delta) of the aglyconic protons of galactosylated chiral alcohols proved to be characteristic of the absolute configuration of the bonded chiral alcohol.