tert-butyl N-[[(3aR,5R,6R,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydropyrano[3,2-d][1,3]thiazol-3a-yl]methyl]carbamate | 1038399-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[[(3aR,5R,6R,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydropyrano[3,2-d][1,3]thiazol-3a-yl]methyl]carbamate
• CAS: 1038399-94-8
• 化学式: C₁₄H₂₄N₂O₆S
• 分子量: 348.42
• InChiKey: TWFOKPIOHHZVPP-ZZPVQSCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[[(3aR,5R,6R,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydropyrano[3,2-d][1,3]thiazol-3a-yl]methyl]carbamate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3aR,5R,6R,7R,7aR)-3a-(aminomethyl)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydropyrano[3,2-d][1,3]thiazole-6,7-diol;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  N-Acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines

  摘要：

  Several C-1 homologated GlcNAc-and GalNAc-thiazolines, as well as a related GalNAc-thiazole, have been prepared. The compounds are analogues of GlcNAc-thiazoline, a potent transition-state-mimicking inhibitor of retaining beta-N-acetylglycosaminidases. Kinetic evaluation of these fused pyranose-heterocycles against the bacterial N-acetylhexosaminidase SpHex suggests active site steric restrictions around the substrate anomeric carbon. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.067
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以72%的产率得到tert-butyl N-[[(3aR,5R,6R,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydropyrano[3,2-d][1,3]thiazol-3a-yl]methyl]carbamate
  参考文献：
  名称：

  N-Acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines

  摘要：

  Several C-1 homologated GlcNAc-and GalNAc-thiazolines, as well as a related GalNAc-thiazole, have been prepared. The compounds are analogues of GlcNAc-thiazoline, a potent transition-state-mimicking inhibitor of retaining beta-N-acetylglycosaminidases. Kinetic evaluation of these fused pyranose-heterocycles against the bacterial N-acetylhexosaminidase SpHex suggests active site steric restrictions around the substrate anomeric carbon. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.067