methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside | 77870-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-3-fluoro-6-methoxyoxan-2-yl]methyl acetate
• CAS: 77870-70-3
• 化学式: C₁₃H₂₀FNO₇
• 分子量: 321.303
• InChiKey: LOAZDUSIBCJPHC-KVSVUVNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2-benzamido-3-O-benzyl-2-deoxy-4,6-di-O-mesyl-α-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 盐酸 、 四丁基氟化铵 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 六甲基磷酰三胺 、 氯仿 、 溶剂黄146 、 乙腈 为溶剂， 反应 58.25h， 生成 methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside
  参考文献：
  名称：

  Hough, Leslie; Penglis, Anna A. E.; Richardson, Anthony C., Canadian Journal of Chemistry, 1981, vol. 59, p. 396 - 405

  摘要：

  DOI：

文献信息

• Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-galactose and their effects on cellular glycosaminoglycan biosynthesis
  作者：Ali Berkin、Walter A. Szarek*、Robert Kisilevsky*

  DOI：10.1016/s0008-6215(00)00049-5

  日期：2000.6

  4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-gala (31) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation to 1 and 9%. respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [C-14]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. (C) 2000 Elsevier Science Ltd. All rights reserved.