2-((3aR,5R,6S,7R,7aR)-6,7-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-3a-yl)acetic acid | 1038399-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3aR,5R,6S,7R,7aR)-6,7-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-3a-yl)acetic acid
• CAS: 1038399-91-5
• 化学式: C₃₈H₆₁NO₆SSi₃
• 分子量: 744.228
• InChiKey: DGEKKCZKCCTQQK-BOMFSUGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  86.58
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-((3aR,5R,6S,7R,7aR)-6,7-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-3a-yl)acetic acid 在 氯甲酸乙酯 、 N,N-二异丙基乙胺 、 sodium azide 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成
  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：

  (叔丁氧基羰基亚甲基)三苯基磷烷 、 N-[(3R,4R,5S,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxooxan-3-yl]ethanethioamide 在 4 A molecular sieve 、 三氟乙酸 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 19.0h， 以48 mg的产率得到2-((3aR,5R,6S,7R,7aR)-6,7-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-3a-yl)acetic 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