benzyl N-[(4aR,6S,7R,8R,8aR)-6-[[(3aR,5S,6R,7S,7aS)-7-[(2S,3R,4R,5R)-4-[(2R,3R,4R,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-prop-2-enoxyoxolan-2-yl]oxy-2-oxo-5-(phenylmethoxycarbonylamino)-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-6-yl]oxy]-8-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate | 1260086-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl N-[(4aR,6S,7R,8R,8aR)-6-[[(3aR,5S,6R,7S,7aS)-7-[(2S,3R,4R,5R)-4-[(2R,3R,4R,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-prop-2-enoxyoxolan-2-yl]oxy-2-oxo-5-(phenylmethoxycarbonylamino)-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-6-yl]oxy]-8-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate
• CAS: 1260086-16-5
• 化学式: C₉₀H₁₃₁N₅O₂₃Si₄
• 分子量: 1763.39
• InChiKey: TVTAFBCBHKOAKJ-COZBZYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.89
• 重原子数：
  122
• 可旋转键数：
  40
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  312
• 氢给体数：
  5
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  benzyl N-[(4aR,6S,7R,8R,8aR)-6-[[(3aR,5S,6R,7S,7aS)-7-[(2S,3R,4R,5R)-4-[(2R,3R,4R,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-prop-2-enoxyoxolan-2-yl]oxy-2-oxo-5-(phenylmethoxycarbonylamino)-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-6-yl]oxy]-8-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate 在 lithium hydroxide 作用下， 以 水 为溶剂， 以63%的产率得到2"-O-allyl-4',6'-O-benzylidene-tetra-O-tert-butyldimethyIsiIanyloxy-tetra-N-benzyloxycarbonyl paromomycin
  参考文献：
  名称：

  Structure-based design, synthesis and A-site rRNA co-crystal complexes of novel amphiphilic aminoglycoside antibiotics with new binding modes: A synergistic hydrophobic effect against resistant bacteria

  摘要：

  Incorporation of an hydrophobic (phenethylamino) ethyl ether at C2 '' of N1-(HABA)-3',4'-dideoxyparomomycin led to a novel analog with an excellent antibacterial profile against a host of resistant bacteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.084
• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到benzyl N-[(4aR,6S,7R,8R,8aR)-6-[[(3aR,5S,6R,7S,7aS)-7-[(2S,3R,4R,5R)-4-[(2R,3R,4R,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-prop-2-enoxyoxolan-2-yl]oxy-2-oxo-5-(phenylmethoxycarbonylamino)-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-6-yl]oxy]-8-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate
  参考文献：
  名称：

  Structure-based design, synthesis and A-site rRNA co-crystal complexes of novel amphiphilic aminoglycoside antibiotics with new binding modes: A synergistic hydrophobic effect against resistant bacteria

  摘要：

  Incorporation of an hydrophobic (phenethylamino) ethyl ether at C2 '' of N1-(HABA)-3',4'-dideoxyparomomycin led to a novel analog with an excellent antibacterial profile against a host of resistant bacteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.084