allyl 2,4-diazido-2,4,6-trideoxy-α-L-mannopyranoside | 676127-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,4-diazido-2,4,6-trideoxy-α-L-mannopyranoside
• 英文别名: (2S,3R,4R,5R,6R)-3,5-diazido-2-methyl-6-prop-2-enoxyoxan-4-ol
• CAS: 676127-64-3
• 化学式: C₉H₁₄N₆O₃
• 分子量: 254.249
• InChiKey: TUKAZIYNNDBDJM-OFPUPOEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 2,4-diazido-2,4,6-trideoxy-α-L-mannopyranoside 在 吡啶 、 18-冠醚-6 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4S,5R,6S)-2-Allyloxy-3,5-diazido-6-methyl-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018
• 作为产物：
  描述：

  allyl α-L-fucopyranoside 在 吡啶 、 甲醇 、 sodium azide 、 18-冠醚-6 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.0h， 生成 allyl 2,4-diazido-2,4,6-trideoxy-α-L-mannopyranoside
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018

文献信息

• 2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products
  作者：Anna Banaszek、Vladimir Zaitsev

  DOI：10.1016/j.tetasy.2003.11.018

  日期：2004.1

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.