N-phenylethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-furanuronamide | 1227850-69-2

• 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: N-phenylethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-furanuronamide
• 英文别名: (3aR,5S,6R,6aR)-2,2-dimethyl-N-(2-phenylethyl)-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide
• CAS: 1227850-69-2
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: NYZGKMQEOSAQCV-ITTUMRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-phenylethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-furanuronamide 在 吡啶 、 sodium azide 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 5-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-(2-phenylethyl)tetrazole
  参考文献：
  名称：

  Benzotriazole-Mediated Facile Synthesis of Novel Glycosyl Tetrazole

  摘要：

  A facile, simple, and high-yielding synthetic protocol for novel glycosyl tetrazoles has been devised from different carbohydrate-containing amides using benzotriazole methodology under mild reaction condition.

  DOI：

  10.1080/07328303.2011.652790
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-furanuronyl benzotriazole 、 2-苯乙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到N-phenylethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-furanuronamide
  参考文献：
  名称：

  Facile Synthesis of Novel Glycosyl Carboxamide with Sugar in Furanose and Pyranose form Using Benzotriazole Methodology

  摘要：

  There is an increased demand for significant amounts of carbohydrate based molecules for complete biological, medicinal, and pharmacological investigations where tremendous efforts have been made to develop novel and facile procedure for the synthesis of glycoconjugates and diverse carboxamides. Limitations with the common approaches for amide bond formation, including use of hazardous chemicals, long reaction times, low reaction yields, frequently require strong basic catalysts, strictly anhydrous conditions, harsh reaction conditions, expensive and limited availability of coupling materials, and moreover the less stability of activated acids warrant the search of a simple, short, and high yielding amide bond synthetic methodology. Herein, a facile and high yielding synthesis of novel glycosyl carboxamide with both furanose and pyranose sugar using benzotriazole methodology has been developed under mild conditions.

  DOI：

  10.2174/157017810790796363

文献信息

• Diacetoxyiodobenzene Mediated One-Pot Synthesis of Diverse Carboxamides from Aldehydes
  作者：Virendra Prasad、Raju R. Kale、Bhuwan B. Mishra、Dhananjay Kumar、Vinod K. Tiwari

  DOI：10.1021/ol3012315

  日期：2012.6.15

  A novel, one-pot, and highly facile protocol has been devised for an easy access of a series of novel glycosyl carboxamides from aldehydes using diacetoxyiodobenzene in the presence of ionic liquid at ambient temperature.
• Facile Synthesis of Novel Glycosyl Carboxamide with Sugar in Furanose and Pyranose form Using Benzotriazole Methodology
  作者：Raju Kale、Virendra Prasad、Vinod Tiwari

  DOI：10.2174/157017810790796363

  日期：2010.3.1

  There is an increased demand for significant amounts of carbohydrate based molecules for complete biological, medicinal, and pharmacological investigations where tremendous efforts have been made to develop novel and facile procedure for the synthesis of glycoconjugates and diverse carboxamides. Limitations with the common approaches for amide bond formation, including use of hazardous chemicals, long reaction times, low reaction yields, frequently require strong basic catalysts, strictly anhydrous conditions, harsh reaction conditions, expensive and limited availability of coupling materials, and moreover the less stability of activated acids warrant the search of a simple, short, and high yielding amide bond synthetic methodology. Herein, a facile and high yielding synthesis of novel glycosyl carboxamide with both furanose and pyranose sugar using benzotriazole methodology has been developed under mild conditions.
• Benzotriazole-Mediated Facile Synthesis of Novel Glycosyl Tetrazole
  作者：Raju R. Kale、Virendra Prasad、Divya Kushwaha、Vinod K. Tiwari

  DOI：10.1080/07328303.2011.652790

  日期：2012.2

  A facile, simple, and high-yielding synthetic protocol for novel glycosyl tetrazoles has been devised from different carbohydrate-containing amides using benzotriazole methodology under mild reaction condition.