(2S,3R,4R)-5-(dimethylamino)-3-[(dimethylamino)methyl]pentane-1,2,3,4-tetrol | 1407517-80-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3R,4R)-5-(dimethylamino)-3-[(dimethylamino)methyl]pentane-1,2,3,4-tetrol
• CAS: 1407517-80-9
• 化学式: C₁₀H₂₄N₂O₄
• 分子量: 236.312
• InChiKey: DOASUCQOYGYHIB-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 在 palladium 10% on activated carbon 、 氢气 作用下， 60.0 ℃ 、101.33 kPa 条件下， 反应 144.0h， 以63%的产率得到(2S,3R,4R)-5-(dimethylamino)-3-[(dimethylamino)methyl]pentane-1,2,3,4-tetrol
  参考文献：
  名称：

  Nitroso-Dienophile Additions to Dendralenes: A Short Synthesis of Branched Aminosugars

  摘要：

  The first heteroatom-based dienophile cycloadditions to cross-conjugated alkenes ([n]dendralenes) are reported. Nitroso-dienophiles undergo smooth single and double Diels-Alder additions to the parent dendralenes with orientational regio- and stereoselectivity and, notably, with reactivity that depends upon the parity of the [n]dendralene. The first crystal structure of a cross-conjugated hexaene is reported. Vasella's nitroso-sugar reagent gives a highly enantiomerically enriched double cycloadduct with [3]dendralene. This bicyclic oxazine is successively dihydroxylated and then ring-opened to form a branched chain diamino tetrol.

  DOI：

  10.1021/ol302619r

文献信息

• Nitroso-Dienophile Additions to Dendralenes: A Short Synthesis of Branched Aminosugars
  作者：Ruomeng Wang、Gomotsang Bojase、Anthony C. Willis、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1021/ol302619r

  日期：2012.11.16

  The first heteroatom-based dienophile cycloadditions to cross-conjugated alkenes ([n]dendralenes) are reported. Nitroso-dienophiles undergo smooth single and double Diels-Alder additions to the parent dendralenes with orientational regio- and stereoselectivity and, notably, with reactivity that depends upon the parity of the [n]dendralene. The first crystal structure of a cross-conjugated hexaene is reported. Vasella's nitroso-sugar reagent gives a highly enantiomerically enriched double cycloadduct with [3]dendralene. This bicyclic oxazine is successively dihydroxylated and then ring-opened to form a branched chain diamino tetrol.