2''-O-allyl-tetra-tert-butyldimethylsilanyloxy-penta-N-benzyloxycarbonyl-3',4'-dideoxy paromomycin | 940286-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2''-O-allyl-tetra-tert-butyldimethylsilanyloxy-penta-N-benzyloxycarbonyl-3',4'-dideoxy paromomycin
• 英文别名: benzyl N-[(2R,3R,4R,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(2R,3R,4R,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[(1R,2R,3S,5R,6S)-2-[(2R,3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxycarbonylamino)oxan-2-yl]oxy-6-hydroxy-3,5-bis(phenylmethoxycarbonylamino)cyclohexyl]oxy-4-prop-2-enoxyoxolan-3-yl]oxy-6-(phenylmethoxycarbonylaminomethyl)oxan-3-yl]carbamate
• CAS: 940286-37-3
• 化学式: C₉₀H₁₃₅N₅O₂₂Si₄
• 分子量: 1751.42
• InChiKey: QPOYMAAZDYQJTF-UVDPVZGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.36
• 重原子数：
  121
• 可旋转键数：
  44
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  313
• 氢给体数：
  6
• 氢受体数：
  22

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2''-O-allyl-5",6'-O-bis-tert-butyldimethylsilanyloxy-penta-N-benzyloxycarbonyl-3',4'-dideoxy paromomycin 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到2''-O-allyl-tetra-tert-butyldimethylsilanyloxy-penta-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

文献信息

• WO2007/64954
  申请人：——

  公开号：——

  公开（公告）日：——