ethyl 2,3,6-tri-O-benzyl-4-O-picolinyl-1-thio-β-D-glucopyranoside | 1415590-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,6-tri-O-benzyl-4-O-picolinyl-1-thio-β-D-glucopyranoside
• 英文别名: 2-[[(2R,3R,4S,5R,6S)-6-ethylsulfanyl-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]pyridine
• CAS: 1415590-55-4
• 化学式: C₃₅H₃₉NO₅S
• 分子量: 585.764
• InChiKey: GQRZAVRSKBHFHA-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 ethyl 2,3,6-tri-O-benzyl-4-O-picolinyl-1-thio-β-D-glucopyranoside 在 DMTST 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,6-tri-O-benzyl-4-O-picolinyl-β-D-glucopyranosyl)-α-D-glucopyranoside 、 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,6-tri-O-benzyl-4-O-picolinyl-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
• 作为产物：
  描述：

  2-(溴甲基)吡啶氢溴酸盐 、 乙基 2,3,6-O-三苄基-beta-D-硫代吡喃葡萄糖苷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.5h， 以88%的产率得到ethyl 2,3,6-tri-O-benzyl-4-O-picolinyl-1-thio-β-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

• Effect of Remote Picolinyl and Picoloyl Substituents on the Stereoselectivity of Chemical Glycosylation
  作者：Jagodige P. Yasomanee、Alexei V. Demchenko

  DOI：10.1021/ja307355n

  日期：2012.12.12

  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.