(3Z)-3-[(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]thiazol-2-ylidene]-1,1,1-trifluoropropan-2-one | 944070-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3Z)-3-[(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]thiazol-2-ylidene]-1,1,1-trifluoropropan-2-one
• CAS: 944070-45-5
• 化学式: C₁₀H₁₂F₃NO₅S
• 分子量: 315.27
• InChiKey: ONDOILBLNXDTHM-IEFRBTRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3Z)-3-[(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]thiazol-2-ylidene]-1,1,1-trifluoropropan-2-one 、 乙酸酐 在 吡啶 作用下， 反应 2.0h， 以81%的产率得到[(2Z,3aR,5R,6S,7R,7aR)-1-acetyl-6,7-diacetyloxy-2-(3,3,3-trifluoro-2-oxopropylidene)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate
  参考文献：
  名称：

  Tautomeric Modification of GlcNAc-Thiazoline

  摘要：

  The potent O-GlcNAcase (OGA) inhibitor GlcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (X-n = D-3, F, N-3, OH, SMe, COCF3, CF3). Several functionalized GlcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

  DOI：

  10.1021/ol0706814
• 作为产物：
  描述：

  [(2Z,3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-(3,3,3-trifluoro-2-oxopropylidene)-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 以100%的产率得到(3Z)-3-[(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]thiazol-2-ylidene]-1,1,1-trifluoropropan-2-one
  参考文献：
  名称：

  Tautomeric Modification of GlcNAc-Thiazoline

  摘要：

  The potent O-GlcNAcase (OGA) inhibitor GlcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (X-n = D-3, F, N-3, OH, SMe, COCF3, CF3). Several functionalized GlcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

  DOI：

  10.1021/ol0706814