N-((2S,3R,4R,5S,6R)-4-Allyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-2-iodo-benzamide | 693810-54-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2S,3R,4R,5S,6R)-4-Allyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-2-iodo-benzamide
• CAS: 693810-54-7
• 化学式: C₁₇H₂₂INO₆
• 分子量: 463.269
• InChiKey: YVDNHWLGSNXZAG-IETPZCKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  97.25
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,4R,5S,6R)-4-Allyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-2-iodo-benzamide 在 氢氧化钾 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (1R,14R,15S,16R,18S,19R,32R,33S,34R,36S)-18,36-dimethoxy-15,33-bis(phenylmethoxy)-16,34-bis(phenylmethoxymethyl)-13,17,31,35-tetraoxa-2,20-diazapentacyclo[30.4.0.04,9.014,19.022,27]hexatriaconta-4,6,8,22,24,26-hexaene-3,21-dione
  参考文献：
  名称：

  A new 20-membered macrocyclic dilactam: an unexpected product of a tri-n-butyltin hydride-mediated radical reaction

  摘要：

  The tri-n-butyltin hydride-mediated reaction of methyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-(2-iodobenzoylamino)-alpha-D-glucopyranoside affords an unexpected benzomacrodilactam. The structure of this new 20-membered macrocyclic dilactam has been elucidated by electrospray mass and tandem mass spectrometry (ESI-MS/MS) and by H-1, C-13 NMR spectroscopy, COSY, TOCSY, HMQC and HMBC experiments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.116
• 作为产物：
  描述：

  N-((4aR,6S,7R,8R,8aS)-8-Allyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2-iodo-benzamide 在 盐酸 作用下， 以 丙酮 为溶剂， 以73%的产率得到N-((2S,3R,4R,5S,6R)-4-Allyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-2-iodo-benzamide
  参考文献：
  名称：

  A new 20-membered macrocyclic dilactam: an unexpected product of a tri-n-butyltin hydride-mediated radical reaction

  摘要：

  The tri-n-butyltin hydride-mediated reaction of methyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-(2-iodobenzoylamino)-alpha-D-glucopyranoside affords an unexpected benzomacrodilactam. The structure of this new 20-membered macrocyclic dilactam has been elucidated by electrospray mass and tandem mass spectrometry (ESI-MS/MS) and by H-1, C-13 NMR spectroscopy, COSY, TOCSY, HMQC and HMBC experiments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.116