4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosylbenzamide | 1233499-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosylbenzamide
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-benzamido-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1233499-50-7
• 化学式: C₁₇H₁₉NO₆
• 分子量: 333.341
• InChiKey: RMJMGZOONYVSJD-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酰胺 、 乙酰化葡萄烯糖 在 zinc trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 12.0h， 以40%的产率得到
  参考文献：
  名称：

  Zn(II) Triflate-CatalyzedN-Glycosylation: Synthesis of Sulfonamide and Amide Functionalized 2,3-Unsaturated Glycosides

  摘要：

  GRAPHICAL ABSTRACT[GRAPHICS]A highly efficient and mild method for the synthesis of glycosyl sulfonamides and glycosyl amides from glycal has been described using Zn(OTf)(2) as an economical and environmentally friendly catalyst. Various N-nucleophiles comprising sulfonamides, benzamides, and carbamates were glycosylated with glycals to obtain corresponding 2,3-unsaturated N-glycosides in good yields.

  DOI：

  10.1080/07328303.2015.1018994

文献信息

• A mild and efficient synthetic protocol for Ferrier azaglycosylation promoted by ZnCl2/Al2O3
  作者：Feiqing Ding、Ronny William、Bala Kishan Gorityala、Jimei Ma、Siming Wang、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2010.04.045

  日期：2010.6

  An improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-D-glucal with different N-nucleophiles has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 3,4,6-tri-O-acetyl-D-glucal into 2,3-unsaturated-N-pseudoglycals with good yields and preferential alpha-anomeric selectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation
  作者：Thurpu Raghavender Reddy、Sravanthi Chittela、Sudhir Kashyap

  DOI：10.1016/j.tet.2014.10.024

  日期：2014.12

  An efficient, economical and mild protocol for the synthesis of 2,3-unsaturated-N-glycosides has been developed using ruthenium(III) chloride. The Ferrier azaglycosylation of glycals with various N-nucleophiles such as sulfonamides, benzamides, carbamates and N-substituted sulfonamides proceeded smoothly to afford the corresponding 2,3-unsaturated-N-glycosides or 'N-pseudoglycals' in good yields (64-98%). High alpha-anomeric selectivity was observed with N-substituted sulfonamides such as N-benzyl or N-phenyl sulfonamides under similar conditions. (C) 2014 Elsevier Ltd. All rights reserved.