4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl methanesulfonamide | 1254049-82-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl methanesulfonamide
• 英文别名: 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosylmethansulfonamide；[(2R,3R,6S)-3-acetyloxy-6-(methanesulfonamido)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1254049-82-5
• 化学式: C₁₁H₁₇NO₇S
• 分子量: 307.324
• InChiKey: COUYLHIVGSKSST-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲基磺酰胺 、 D-三乙酰半乳糖烯 在 ruthenium trichloride 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以79%的产率得到4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl methanesulfonamide
  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

• Zn(II) Triflate-Catalyzed<i>N</i>-Glycosylation: Synthesis of Sulfonamide and Amide Functionalized 2,3-Unsaturated Glycosides
  作者：Thurpu Raghavender Reddy、Suresh Kumar Battina、Sudhir Kashyap

  DOI：10.1080/07328303.2015.1018994

  日期：2015.3.24

  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.
• Efficient synthesis of 2,3-unsaturated sulfonamidoglycosides by Amberlyst 15
  作者：Carlos A. Témpera、Pedro A. Colinas、Rodolfo D. Bravo

  DOI：10.1016/j.tetlet.2010.07.076

  日期：2010.10

  Sulfonamidoglycosylation of D-glycals in the presence of Amberlyst 15 proceeded effectively to afford the sulfonamidoglycosides in good to high yields with minimal workup and short reaction times. Two N-glycosyl sulfonamides were tested as inhibitors of tumor cell growth in vitro and showed antiproliferative properties in the micromolar range. (C) 2010 Elsevier Ltd. All rights reserved.