ethyl 2,3,6-tri-O-benzyl-4-O-(pyrid-3-ylmethyl)-1-thio-β-D-glucopyranoside | 1415590-68-9

• 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-(pyrid-3-ylmethyl)-1-thio-β-D-glucopyranoside
• CAS: 1415590-68-9
• 化学式: C₃₅H₃₉NO₅S
• 分子量: 585.764
• InChiKey: LYSQKULOUWJIAA-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  59.04
• 氢给体数：
  0.0
• 氢受体数：
  7.0

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-(pyrid-3-ylmethyl)-1-thio-β-D-glucopyranoside 在 DMTST 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,6-tri-O-benzyl-4-O-(pyrid-3-ylmethyl)-β-glucopyranosyl)-α-D-glucopyranoside 、 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,6-tri-O-benzyl-4-O-(pyrid-3-ylmethyl)-α-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：

  乙基 2,3,6-O-三苄基-beta-D-硫代吡喃葡萄糖苷 、 3-(bromomethyl)pyridine hydrobromide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.5h， 以89%的产率得到ethyl 2,3,6-tri-O-benzyl-4-O-(pyrid-3-ylmethyl)-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