[(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-methylidene-1-(2,2,2-trifluoroacetyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate | 944070-42-2

• 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: [(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-methylidene-1-(2,2,2-trifluoroacetyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate
• CAS: 944070-42-2
• 化学式: C₁₆H₁₈F₃NO₈S
• 分子量: 441.382
• InChiKey: URZSHTIQTCGTOE-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-methylidene-1-(2,2,2-trifluoroacetyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate 在 甲醇 、 sodium methylate 、 过氧化苯甲酰 作用下， 以 乙腈 为溶剂， 反应 1.33h， 生成 (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-(2,2,2-trifluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
  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：

  (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole 、 三氟乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到[(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-methylidene-1-(2,2,2-trifluoroacetyl)-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