4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl-N-p-nitrophenylsulfonamide | 764674-79-5

• 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-enopyranosyl-N-p-nitrophenylsulfonamide
• 英文别名: 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl-4'-nitrophenylsulfonamide；[(2R,3S,6S)-3-acetyloxy-6-[(4-nitrophenyl)sulfonylamino]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 764674-79-5
• 化学式: C₁₆H₁₈N₂O₉S
• 分子量: 414.393
• InChiKey: WUWAOOVFZWKAOB-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  对硝基苯磺酰氯 在 ruthenium trichloride 、 氨 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl-N-p-nitrophenylsulfonamide 、 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl-N-p-nitrophenylsulfonamide
  参考文献：
  名称：

  Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation

  摘要：

  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.

  DOI：

  10.1016/j.tet.2014.10.024

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.
• An eco-friendly tandem tosylation/Ferrier N -glycosylation of amines catalyzed by Er(OTf) 3 in 2-MeTHF
  作者：Monica Nardi、Natividad Herrera Cano、Antonio De Nino、Maria Luisa Di Gioia、Loredana Maiuolo、Manuela Oliverio、Ana Santiago、Diletta Sorrentino、Antonio Procopio

  DOI：10.1016/j.tetlet.2017.03.047

  日期：2017.5

  Er(OTf)(3) in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-d-glucal and different nucleophiles affording good results in a short time. (C) 2017 Published by Elsevier Ltd.