methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside | 1415590-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside
• CAS: 1415590-89-4
• 化学式: C₆₁H₆₃NO₁₂
• 分子量: 1002.17
• InChiKey: AGPYAVXQAYBWJB-NJQPWPGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.86
• 重原子数：
  74.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  131.49
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  2-吡啶甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 8.25h， 生成 methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Effect of Remote Picolinyl and Picoloyl Substituents on the Stereoselectivity of Chemical Glycosylation

  摘要：

  O-Picolinyl and O-picoloyl groups at remote positions (C-3, C-4, and C-6) can mediate glycosylation reactions by providing high or even complete facial selectivity for the attack of the glycosyl acceptor. The set of data presented herein offers a strong evidence of the intermolecular H-bond tethering between the glycosyl donor and glycosyl acceptor counterparts while providing a practical new methodology for the synthesis of either 1,2-cis or 1,2-trans linkages. Challenging glycosidic linkages including alpha-gluco, beta-manno, and beta-rhamno have seen obtained with high or complete stereocontrol.

  DOI：

  10.1021/ja307355n

文献信息

• Hydrogen-Bond-Mediated Aglycone Delivery (HAD): A Highly Stereoselective Synthesis of 1,2-<i>cis</i>α-<scp>D</scp>-Glucosides from Common Glycosyl Donors in the Presence of Bromine
  作者：Jagodige P. Yasomanee、Alexei V. Demchenko

  DOI：10.1002/chem.201406589

  日期：2015.4.20

  H‐bond mediated aglycone delivery (HAD) method recently introduced by our laboratory. At first it was noticed that high α‐stereoselectivity is only obtained with S‐ethyl glycosyl donors and only in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), in high dilution, and low temperature. Combining the mechanistic studies of the HAD reaction and bromine‐promoted glycosylations

  本文描述的是我们实验室最近引入的由吡啶甲酰基保护基辅助的H键介导的糖苷配基递送（HAD）方法的扩展。最初，人们注意到只有在高稀释度和低温下，仅在S-乙基糖基供体和三氟甲磺酸二甲基（甲硫基）ulf存在下，才能获得高α-立体选择性。将HAD反应的机理研究与溴促进的糖基化结合起来，可以设计出一种非常有效的方法，该方法可以对几乎所有常见的离去基团（S-苯基，S-甲苯基，S / O-亚氨酸酯）进行高度立体选择性的α-糖基化。在常规浓度和环境温度下。