1,5-anhydro-4-azido-2,6-dideoxy-D-threo-hex-1-enit-ulose | 355131-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,5-anhydro-4-azido-2,6-dideoxy-D-threo-hex-1-enit-ulose
• 英文别名: (2R,3S)-3-azido-2-methyl-2,3-dihydropyran-4-one
• CAS: 355131-39-4
• 化学式: C₆H₇N₃O₂
• 分子量: 153.14
• InChiKey: XSYDZZGDMRXQSG-XINAWCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4-azido-2,6-dideoxy-D-threo-hex-1-enit-ulose 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 methyl 4-azido-4,6-dideoxy-3-C-methyl-α-D-talo-pyranoside
  参考文献：
  名称：

  An expedient synthesis of d-callipeltose

  摘要：

  Methyl D-callipeltose 12 and D-callipeltose 4 were synthesized from D-glucal 5 in 10 and 11 steps, respectively. The synthesis features an azide displacement reaction of an alpha -nosyloxy ketone 7 and a highly diastereoselective C-methylation of alpha -azido ketone 8. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00146-x
• 作为产物：
  描述：

  (2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol 在 manganese(IV) oxide 、 叠氮化四丁基铵 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 1,5-anhydro-4-azido-2,6-dideoxy-D-threo-hex-1-enit-ulose
  参考文献：
  名称：

  An expedient synthesis of d-callipeltose

  摘要：

  Methyl D-callipeltose 12 and D-callipeltose 4 were synthesized from D-glucal 5 in 10 and 11 steps, respectively. The synthesis features an azide displacement reaction of an alpha -nosyloxy ketone 7 and a highly diastereoselective C-methylation of alpha -azido ketone 8. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00146-x

文献信息

• An expedient synthesis of d-callipeltose
  作者：Ainoliisa J. Pihko、K.C. Nicolaou、Ari M.P. Koskinen

  DOI：10.1016/s0957-4166(01)00146-x

  日期：2001.4

  Methyl D-callipeltose 12 and D-callipeltose 4 were synthesized from D-glucal 5 in 10 and 11 steps, respectively. The synthesis features an azide displacement reaction of an alpha -nosyloxy ketone 7 and a highly diastereoselective C-methylation of alpha -azido ketone 8. (C) 2001 Elsevier Science Ltd. All rights reserved.