methyl 2,3,4,6-tetrakis(O-(p-bromobenzoyl))-β-D-glucopyranoside | 78950-20-6

• 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))-β-D-glucopyranoside
• 英文别名: Methyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranoside；methyl 2,3,4,6-tetra-O-(p-bromobenzoyl)-β-D-glucopyranoside；methyl β-D-glucopyranoside tetrakis(p-bromobenzoate)；[(2R,3R,4S,5R,6R)-3,4,5-tris[(4-bromobenzoyl)oxy]-6-methoxyoxan-2-yl]methyl 4-bromobenzoate
• CAS: 78950-20-6
• 化学式: C₃₅H₂₆Br₄O₁₀
• 分子量: 926.201
• InChiKey: JYESNPYPYZSTLC-PHZXZDAQSA-N

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

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetrakis(O-(p-bromobenzoyl))-β-D-glucopyranoside 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl 2,3,4,6-tetrakis(O-(p-bromobenzoyl))-α-D-glucopyranoside
  参考文献：
  名称：

  氯化铁，一种用于制备烷基α-吡喃葡萄糖苷的阴离子化催化剂

  摘要：

  已经发现CH 2 Cl 2中的无水FeCl 3可以在室温下以良好的产率和选择性将β-糖吡喃糖苷容易地异构化为其相应的α-端基异构体。乙酰基和苯甲酰基保护的氧糖产生了最好的结果。

  DOI：

  10.1016/s0040-4039(00)74242-0
• 作为产物：
  描述：

  甲醇 、 2,3,4,6-Tetrakis-O-(p-bromobenzoyl)-α-D-glucopyranosyl bromide 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到methyl 2,3,4,6-tetrakis(O-(p-bromobenzoyl))-β-D-glucopyranoside
  参考文献：
  名称：

  CD and 1H NMR Study of the Rotational Population Dependence of the Hydroxymethyl Group in .beta. Glucopyranosides on the Aglycon and Its Absolute Configuration

  摘要：

  The rotamer population around the C5-C6 bond of chiral and nonchiral alkyl P-D-glucopyranoside derivatives proved to be dependent on the structure of the aglycon; the population of the gg and gt rotamers decreased and increased, respectively, as the pK(a) of the aglycon increased, whereas the rs tg population remained almost constant. In addition, the rotamer populations correlate with the absolute configuration of the aglyconic carbons, namely, higher CD A values and smaller (3)J(H5,H6R) coupling constants are obtained for the (R)-alkyl glucopyranosides than for their (S)-alkyl glucopyranoside counterparts, as the result of increased and decreased gg and gt populations, respectively. The results show a clear relationship between the rotamer distributions and the stereoelectronic exo-anomeric effect. Asa consequence of these findings the absolute configuration of secondary alcohols can be determined, a single enantiomer being necessary for this purpose.

  DOI：

  10.1021/jo00113a038

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，
• A CD-Spectroscopic Alternative to Methylation Analysis of Oligosaccharides: Reference Spectra for Identification of Chromophoric Glycopyranoside Derivatives
  作者：William T. Wiesler、Nikolina Berova、Makoto Ojika、Harold V. Meyers、Mayland Chang、Peng Zhou、Lee-Chiang Lo、Masatake Niwa、Reiji Takeda、Koji Nakanishi

  DOI：10.1002/hlca.19900730302

  日期：1990.5.2

  conversion of oligosaccharides to monosaccharide subunits bearing 4-bromobenzoate and 4-methoxycinnamate chromophores have been developed based on acetolysis/bromination reactions for glycosidic cleavage of per (bromobenzoylated) oligosaccharides. The method offers an alternative means to conventional methylation analysis of oligosaccharides.

  提出了一种用于鉴定寡糖中单糖单元及其键合的微型方法。糖成分通过发色降解产物的UV和CD光谱进行鉴定。提供了大约150种不同的吡喃葡萄糖苷成分的CD光谱数据，以用作鉴定未知衍生物的参考光谱。基于对每个（溴苯甲酰化）寡糖进行糖苷裂解的乙酰分解/溴化反应，已经开发了将寡糖转化为带有4-溴苯甲酸酯和4-甲氧基肉桂酸酯发色团的单糖亚基的方法。该方法为常规的寡糖甲基化分析提供了另一种方法。
• A New Coumarin Glucoside from Daphne arisanensis.
  作者：Masatake NIWA、Hidetoshi SUGINO、Shigeki TAKASHIMA、Tatsuko SAKAI、Yang-Chang WU、Tian-Sheng WU、Chan-Sheng KUOH

  DOI：10.1248/cpb.39.2422

  日期：——

  A new coumarin glucoside named daphneside was isolated along with two known coumarin glucosides, daphnin and daphnetin-8-glucoside, and two known phenylpropanoid glucosides, syringin and syringinoside, from a water-soluble fraction of Daphne arisanensis HAYATA (Thymelaeaceae) collected in Taiwan. The structure of daphneside was elucidated by spectroscopic and chemical methods.

  从台湾采集的 Daphne arisanensis HAYATA（百日草科）的水溶性馏分中分离出了一种名为 daphneside 的新香豆素葡萄糖苷，以及两种已知的香豆素葡萄糖苷（daphnin 和 daphnetin-8-葡萄糖苷）和两种已知的苯丙酮葡萄糖苷（syringin 和 syringinoside）。通过光谱和化学方法阐明了 Daphneside 的结构。
• Microscale glycosidic cleavage of oligosaccharide bromobenzoates for circular dichroism analysis
  作者：Makoto Ojika、Harold V. Meyers、Mayland Chang、Koji Nakanishi

  DOI：10.1021/ja00206a042

  日期：1989.11

  La degradation chimique de la digitonine avec une solution de bromure de l'acide bromo acetique donne des halogenures d'hexo (ou pento) pyranosyles bromobenzoyles ou bromoacetyles qui sont ensuite transformes en O-methyl-1 hexo (ou pento) pyranosides bromobenzoyles et methoxy-4 cinnamoyles

  La 降解 chimique de la digitonine avec une 溶液 de bromure de l'acide bromo acetique donne des haloures d'hexo (ou pento) pyranosyles bromobenzoyles ou bromoacetyles quisont ensuitetransformes en O-methyl-1 hexo (ou pento) pyranosides et bromobenzoyles -4 肉桂
• KAWAI, HIDEAKI;KUROYANAGI, MASANORI;UMEHARA, KAORU;UENO, AKIRA;SATAKE, MO+, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4769-4775
  作者：KAWAI, HIDEAKI、KUROYANAGI, MASANORI、UMEHARA, KAORU、UENO, AKIRA、SATAKE, MO+

  DOI：——

  日期：——