(4-methyl-2-sulfanylidene-1,3-thiazol-3-yl) (3R,4R,5S)-4-acetamido-5-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yloxycyclohexene-1-carboxylate | 1373702-86-3

• 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: (4-methyl-2-sulfanylidene-1,3-thiazol-3-yl) (3R,4R,5S)-4-acetamido-5-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yloxycyclohexene-1-carboxylate
• CAS: 1373702-86-3
• 化学式: C₂₃H₃₅N₃O₆S₂
• 分子量: 513.679
• InChiKey: XKBFQGHTFDCGTK-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4-methyl-2-sulfanylidene-1,3-thiazol-3-yl) (3R,4R,5S)-4-acetamido-5-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yloxycyclohexene-1-carboxylate 在 trifluoroiodoethane 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以164 mg的产率得到4-acetamido-5-(tert-butoxycarbonyl)amino-3-(1-ethylpropoxy)-1-iodo-1-cyclohexene
  参考文献：
  名称：

  Tamiphosphor monoesters as effective anti-influenza agents

  摘要：

  Oseltamivir is a potent neuraminidase inhibitor for influenza treatment. By replacing the carboxylate group in oseltamivir with phosphonate monoalkyl ester, a series of tamiphosphor derivatives were synthesized and shown to exhibit high inhibitory activities against influenza viruses. Our molecular modeling experiments revealed that influenza virus neuraminidase contains a 371-cavity near the S1-site to accommodate the alkyl substituents of tamiphosphor monoesters to render appreciable hydrophobic interactions for enhanced affinity. Furthermore, guanidino-tamiphosphor (TPG) monoesters are active to the oseltamivir-resistant mutant. TPG monohexyl ester 4e having a more lipophilic alkyl substituent showed better cell permeability and intestinal absorption than the corresponding monoethyl ester 4c, but both compounds showed similar bioavailability. Intranasal administration of TPG monoesters at low dose greatly improved the survival rate of mice infected with lethal dose of H1N1 influenza virus, whereas 4c provided better protection of the infected mice than oseltamivir and other phosphonate congeners by oral administration. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.082
• 作为产物：
  描述：

  磷酸奥司他韦 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.75h， 生成 (4-methyl-2-sulfanylidene-1,3-thiazol-3-yl) (3R,4R,5S)-4-acetamido-5-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yloxycyclohexene-1-carboxylate
  参考文献：
  名称：

  达菲的正式合成：达菲转化为磷酰胺

  摘要：

  柴的第三代中间的短，对映体，合成而形成（ - ） -奥司他韦磷酸盐（达菲®）已在八个步骤与使用便宜的起始原料已经实现。已经完成了通过方氏的tamiphosphor中间体将tamiflu转化为tamiphosphor的正式合成途径。 水解-环氧-氧化-酰胺-对映选择性

  DOI：

  10.1055/s-0031-1290356