(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(tetradecanoyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole | 1147271-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(tetradecanoyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole
• CAS: 1147271-66-6
• 化学式: C₂₂H₃₉NO₅S
• 分子量: 429.621
• InChiKey: QHAUPWFZKWPTKY-MSEOUXRUSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  557.7±50.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  29.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  88.35
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(tetradecanoyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole 、 乙酸酐 在 吡啶 作用下， 生成 (3aR,5R,6S,7R,7aR)-2-methyl-5-((tetradecanoyloxy)methyl)-3a,6,7,7a-tetrahydro-5H-pyrano[3,2-d]thiazole-6,7-diyl diacetate
  参考文献：
  名称：

  GlcNAc-Thiazoline conformations

  摘要：

  The title compound, a powerful inhibitor of retaining N-acetylhexosaminidases, can move freely among three pyranose solution conformations of similar energy-two twist boats and the (4)C(1) chair-as revealed by NMR, calculational, and crystallographic studies. It binds in the enzyme active site only in the pseudo-(4)C(1) conformation, however, in which it most closely resembles the hypothetical bound substrate transition state, a (4)E sofa that is approximately trigonal bipyramidal at the anomeric carbon. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.066
• 作为产物：
  描述：

  肉豆蔻酸 、 (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以21%的产率得到(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(tetradecanoyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole
  参考文献：
  名称：

  GlcNAc-Thiazoline conformations

  摘要：

  The title compound, a powerful inhibitor of retaining N-acetylhexosaminidases, can move freely among three pyranose solution conformations of similar energy-two twist boats and the (4)C(1) chair-as revealed by NMR, calculational, and crystallographic studies. It binds in the enzyme active site only in the pseudo-(4)C(1) conformation, however, in which it most closely resembles the hypothetical bound substrate transition state, a (4)E sofa that is approximately trigonal bipyramidal at the anomeric carbon. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.066