[(3S,4S,5S,6S)-4,5-bis(2,2-dimethylpropanoyloxy)-6-[(1R)-2-methoxy-2-oxo-1-[(2,2,2-trifluoroacetyl)amino]ethyl]oxan-3-yl] 2,2-dimethylpropanoate | 338974-70-2

• 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: [(3S,4S,5S,6S)-4,5-bis(2,2-dimethylpropanoyloxy)-6-[(1R)-2-methoxy-2-oxo-1-[(2,2,2-trifluoroacetyl)amino]ethyl]oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 338974-70-2
• 化学式: C₂₅H₃₈F₃NO₁₀
• 分子量: 569.573
• InChiKey: XIHXSFDBWCRTEH-XFIYOXNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(3S,4S,5S,6S)-4,5-bis(2,2-dimethylpropanoyloxy)-6-[(1R)-2-methoxy-2-oxo-1-[(2,2,2-trifluoroacetyl)amino]ethyl]oxan-3-yl] 2,2-dimethylpropanoate 在 sodium tetrahydroborate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthetic analogues of SB-219383. Novel C-glycosyl peptides as inhibitors of tyrosyl tRNA synthetase

  摘要：

  Novel inhibitors of bacterial tyrosyl tRNA synthetase have been synthesised in which the cyclic hydroxylamine moiety of SE-219383 is replaced by C-pyranosyl derivatives. Potent and selective inhibition of bacterial tyrosyl tRNA synthetase was obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00039-7
• 作为产物：
  描述：

  tetrapivaloyl-α-L(+)-arabinose 在 氢溴酸 、 溶剂黄146 、 zinc dibromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 [(3S,4S,5S,6S)-4,5-bis(2,2-dimethylpropanoyloxy)-6-[(1R)-2-methoxy-2-oxo-1-[(2,2,2-trifluoroacetyl)amino]ethyl]oxan-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthetic analogues of SB-219383. Novel C-glycosyl peptides as inhibitors of tyrosyl tRNA synthetase

  摘要：

  Novel inhibitors of bacterial tyrosyl tRNA synthetase have been synthesised in which the cyclic hydroxylamine moiety of SE-219383 is replaced by C-pyranosyl derivatives. Potent and selective inhibition of bacterial tyrosyl tRNA synthetase was obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00039-7