(S)-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-((3aS,4R,6R,7aR)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-acetic acid butyl ester | 338975-16-9

• 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: (S)-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-((3aS,4R,6R,7aR)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-acetic acid butyl ester
• 英文别名: butyl (2S)-2-[(3aS,4R,6R,7aR)-2,2,4-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2-[[(2S)-2-(phenylmethoxycarbonylamino)-3-(4-phenylmethoxyphenyl)propanoyl]amino]acetate
• CAS: 338975-16-9
• 化学式: C₃₉H₄₈N₂O₉
• 分子量: 688.818
• InChiKey: OWKGFRLUKHMLEI-UJPATFRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-((3aS,4R,6R,7aR)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-acetic acid butyl ester 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 [(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-((2R,4R,5R,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid butyl ester
  参考文献：
  名称：

  Potent synthetic inhibitors of tyrosyl tRNA synthetase derived from C-pyranosyl analogues of SB-219383

  摘要：

  Novel pyranosyl analogues of SE-219383 have been synthesised to elucidate the structure-activity relationships around the pyran ring. Analogues with highly potent stereoselective and bacterioselective inhibition of bacterial tyrosyl tRNA synthetase have been identified. A major reduction in the overall polarity of the molecule can be tolerated without loss of the nanomolar level of inhibition. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00040-3
• 作为产物：
  描述：

  O-苯基-N-叔丁基羰基-L-酪氨酸 在 吡啶 、 N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 56.0h， 生成 (S)-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-((3aS,4R,6R,7aR)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-acetic acid butyl ester
  参考文献：
  名称：

  Potent synthetic inhibitors of tyrosyl tRNA synthetase derived from C-pyranosyl analogues of SB-219383

  摘要：

  Novel pyranosyl analogues of SE-219383 have been synthesised to elucidate the structure-activity relationships around the pyran ring. Analogues with highly potent stereoselective and bacterioselective inhibition of bacterial tyrosyl tRNA synthetase have been identified. A major reduction in the overall polarity of the molecule can be tolerated without loss of the nanomolar level of inhibition. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00040-3

文献信息

• Potent synthetic inhibitors of tyrosyl tRNA synthetase derived from C-pyranosyl analogues of SB-219383
  作者：Richard L Jarvest、John M Berge、Pamela Brown、Dieter W Hamprecht、David J McNair、Lucy Mensah、Peter J O'Hanlon、Andrew J Pope

  DOI：10.1016/s0960-894x(01)00040-3

  日期：2001.3

  Novel pyranosyl analogues of SE-219383 have been synthesised to elucidate the structure-activity relationships around the pyran ring. Analogues with highly potent stereoselective and bacterioselective inhibition of bacterial tyrosyl tRNA synthetase have been identified. A major reduction in the overall polarity of the molecule can be tolerated without loss of the nanomolar level of inhibition. (C) 2001 Elsevier Science Ltd. All rights reserved.