(6'-azido-3'-O-benzyl-6'-deoxy-2'4'-di-O-methoxymethyl-α-D-glucopyranosyl)-acetaldehyde | 886552-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6'-azido-3'-O-benzyl-6'-deoxy-2'4'-di-O-methoxymethyl-α-D-glucopyranosyl)-acetaldehyde
• 英文别名: 2-[(2R,3S,4R,5R,6R)-6-(azidomethyl)-3,5-bis(methoxymethoxy)-4-phenylmethoxyoxan-2-yl]acetaldehyde
• CAS: 886552-37-0
• 化学式: C₁₉H₂₇N₃O₇
• 分子量: 409.439
• InChiKey: QEZANFVUHZZJRM-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (6'-azido-3'-O-benzyl-6'-deoxy-2'4'-di-O-methoxymethyl-α-D-glucopyranosyl)-acetaldehyde 在 polymer-bound diphenylphosphine 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 64.0h， 生成 (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-7,9,16,18-tetrakis(methoxymethoxy)-8,17-bis(phenylmethoxy)-19,20-dioxa-3,12-diazatricyclo[13.3.1.16,10]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
• 作为产物：
  描述：

  3-(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)prop-1-ene 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 0.5h， 以65%的产率得到(6'-azido-3'-O-benzyl-6'-deoxy-2'4'-di-O-methoxymethyl-α-D-glucopyranosyl)-acetaldehyde
  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.