(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane | 886552-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane
• 英文别名: (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-7,9,16,18-tetramethoxy-8,17-bis(phenylmethoxy)-19,20-dioxa-3,12-diazatricyclo[13.3.1.16,10]icosane
• CAS: 886552-45-0
• 化学式: C₃₄H₅₀N₂O₈
• 分子量: 614.78
• InChiKey: DLGCBGUOAYJYQB-CCHDLNLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  97.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane 在 钯 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 (1R,6R,7R,8R,9S,10R,15R,16R,17R,18S)-8,17-Dihydroxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  De Novo Synthesis of Sugar-Aza-Crown Ethers via a Domino Staudinger Aza-Wittig Reaction

  摘要：

  A short and highly efficient route to sugar-aza-crown (SAC) ethers has been developed. The key step of the transformation is a one-pot cyclodimerization of C-glycosyl azido aldehydes via a domino Staudinger aza-Wittig reaction. This process allows the preparation of various orthogonally protected SAC ethers, from both alpha- and beta-C-glycosyl azido aldehydes.

  DOI：

  10.1021/jo052489q
• 作为产物：
  描述：

  3-(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methyl-α-D-glucopyranosyl)-1-propene 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 、 polymer-bound diphenylphosphine 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 64.5h， 生成 (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane
  参考文献：
  名称：

  De Novo Synthesis of Sugar-Aza-Crown Ethers via a Domino Staudinger Aza-Wittig Reaction

  摘要：

  A short and highly efficient route to sugar-aza-crown (SAC) ethers has been developed. The key step of the transformation is a one-pot cyclodimerization of C-glycosyl azido aldehydes via a domino Staudinger aza-Wittig reaction. This process allows the preparation of various orthogonally protected SAC ethers, from both alpha- and beta-C-glycosyl azido aldehydes.

  DOI：

  10.1021/jo052489q

文献信息

• De Novo Synthesis of Sugar-Aza-Crown Ethers via a Domino Staudinger Aza-Wittig Reaction
  作者：Mickaël Ménand、Jean-Claude Blais、Jean-Marc Valéry、Juan Xie

  DOI：10.1021/jo052489q

  日期：2006.4.1

  A short and highly efficient route to sugar-aza-crown (SAC) ethers has been developed. The key step of the transformation is a one-pot cyclodimerization of C-glycosyl azido aldehydes via a domino Staudinger aza-Wittig reaction. This process allows the preparation of various orthogonally protected SAC ethers, from both alpha- and beta-C-glycosyl azido aldehydes.