benzyl N-[(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-6-[(2R,3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxycarbonylamino)oxan-2-yl]oxy-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-5-yl]carbamate | 940286-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl N-[(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-6-[(2R,3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxycarbonylamino)oxan-2-yl]oxy-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-5-yl]carbamate
• CAS: 940286-38-4
• 化学式: C₈₃H₁₂₇N₅O₂₁Si₄
• 分子量: 1643.28
• InChiKey: JHOZGNHRTMXOKQ-PIRSGQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.18
• 重原子数：
  113
• 可旋转键数：
  40
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  293
• 氢给体数：
  5
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  benzyl N-[(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-6-[(2R,3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxycarbonylamino)oxan-2-yl]oxy-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-5-yl]carbamate 在 lithium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以88%的产率得到2"-O-allyl-tetra-tert-butyldimethylsilanyloxy-tetra-N-benzyloxycarbonyl-3',4'-dideoxy 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：

  2''-O-allyl-tetra-tert-butyldimethylsilanyloxy-penta-N-benzyloxycarbonyl-3',4'-dideoxy paromomycin 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.0h， 以49%的产率得到benzyl N-[(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-6-[(2R,3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxycarbonylamino)oxan-2-yl]oxy-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-5-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

文献信息

• WO2007/64954
  申请人：——

  公开号：——

  公开（公告）日：——
• 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
  作者：Stephen Hanessian、Kandasamy Pachamuthu、Janek Szychowski、Alexandre Giguère、Eric E. Swayze、Michael T. Migawa、Boris François、Jiro Kondo、Eric Westhof

  DOI：10.1016/j.bmcl.2010.09.084

  日期：2010.12

  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.