[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-hydroxy-6-methyloxan-2-yl]methyl acetate | 483342-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-hydroxy-6-methyloxan-2-yl]methyl acetate
• CAS: 483342-18-3
• 化学式: C₁₅H₂₃NO₉
• 分子量: 361.349
• InChiKey: QXAPGDBWEHNVTL-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-hydroxy-6-methyloxan-2-yl]methyl acetate 在 劳森试剂 、 4-甲基苯磺酸吡啶 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以20%的产率得到(3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2,3a-dimethyl-5,6,7,7a-tetrahydropyrano[3,2-d][1,3]thiazole-6,7-diol
  参考文献：
  名称：

  Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

  摘要：

  Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of Methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected I-C-Me GlcNAc oxazoline, a potential I-C-Me GlcNAc donor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01506-x
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 溶剂黄146 为溶剂， 生成 [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-hydroxy-6-methyloxan-2-yl]methyl acetate
  参考文献：
  名称：

  Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

  摘要：

  Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of Methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected I-C-Me GlcNAc oxazoline, a potential I-C-Me GlcNAc donor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01506-x