2,3,4,6-tetra-O-benzyl-D-mannopyranosyl 2-pyridinecarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl 2-pyridinecarboxylate
• 英文别名: [(3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] pyridine-2-carboxylate
• 化学式: C₄₀H₃₉NO₇
• 分子量: 645.752
• InChiKey: ULYBNVITKIUERT-VZRPCBFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannopyranosyl 2-pyridinecarboxylate 在 copper(ll) bromide 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  在轻度中性条件下，通过螯合辅助活化的吡啶甲酸酯活化糖基氯化物和溴化物的合成。

  摘要：

  已经开发了在温和和中性条件下由吡啶甲酸酯形成糖基氯化物和溴化物的通用方法。台式稳定的吡啶甲酸酯被卤化铜（II）物种活化，以高收率提供具有无痕离去基团的相应产品。通过邻族参与，可通过此途径获得稀有的β糖基氯。另外，可以制备具有先前不易获得的具有不稳定保护基的糖基氯化物。

  DOI：

  10.1021/acs.orglett.0c00078

文献信息

• Glycosyl 2-Pyridinecarboxylate as an Effective Glycosyl Donor: Glycosidation of Mannose, 2-Azidosugar, and 2-Deoxysugar into Disaccharides.
  作者：Hironori FURUKAWA、Kazunori KOIDE、Ken-ichi TAKAO、Susumu KOBAYASHI

  DOI：10.1248/cpb.46.1244

  日期：——

  Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar-type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction.

  使用 2-吡啶甲酸糖基作为糖基供体进行了糖基化反应。2 吡啶甲酸糖基酯是根据远程活化概念的一种变体设计的，通过与温和的路易斯酸（如三酸铜和三酸锡）的双叉配位而活化。这种方法不仅对葡萄糖的糖苷化有效，而且对甘露糖型、2-叠氮糖型和 2-脱氧糖型等其他几种糖的糖苷化也有效。通过该反应还能以极高的产率获得各种二糖。
• Mild Cu(OTf)₂-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group
  作者：Wenjing Ye、Christopher M. Stevens、Peng Wen、Christopher J. Simmons、Weiping Tang

  DOI：10.1021/acs.joc.0c01041

  日期：2020.12.18

  C-glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were devel-oped. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corre-sponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.
• Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions
  作者：Peng Wen、Christopher J. Simmons、Zhi-xiong Ma、Stephanie A. Blaszczyk、Paul G. Balzer、Wenjing Ye、Xiyan Duan、Hao-Yuan Wang、Dan Yin、Christopher M. Stevens、Weiping Tang

  DOI：10.1021/acs.orglett.0c00078

  日期：2020.2.21

  formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting

  已经开发了在温和和中性条件下由吡啶甲酸酯形成糖基氯化物和溴化物的通用方法。台式稳定的吡啶甲酸酯被卤化铜（II）物种活化，以高收率提供具有无痕离去基团的相应产品。通过邻族参与，可通过此途径获得稀有的β糖基氯。另外，可以制备具有先前不易获得的具有不稳定保护基的糖基氯化物。