3,6-Anhydro-5-azido-4-O-benzyl-1,2,5-trideoxy-D-arabino-hex-1-ynitol | 923287-06-3

• 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: 3,6-Anhydro-5-azido-4-O-benzyl-1,2,5-trideoxy-D-arabino-hex-1-ynitol
• 英文别名: (2R,3R,4R)-4-azido-2-ethynyl-3-phenylmethoxyoxolane
• CAS: 923287-06-3
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: ZGBANCILBGDSLP-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-Anhydro-5-azido-4-O-benzyl-1,2,5-trideoxy-D-arabino-hex-1-ynitol 在 palladium on activated charcoal 六甲基磷酰三胺 、 正丁基锂 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 11.0h， 生成 ent-jaspine B
  参考文献：
  名称：

  Total synthesis of pachastrissamine (jaspine B) enantiomers from d-glucose

  摘要：

  Synthesis of both enantiomers of pachastrissamine is described from a common chiral template. The stereoselective construction of the central tetrahydrofuran units was based on the pseudodesymmetrization of a pentodialdo-1,4-furanose derivative taking advantage of the latent symmetry present. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.11.048
• 作为产物：
  描述：

  在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3,6-Anhydro-5-azido-4-O-benzyl-1,2,5-trideoxy-D-arabino-hex-1-ynitol
  参考文献：
  名称：

  Total synthesis of pachastrissamine (jaspine B) enantiomers from d-glucose

  摘要：

  Synthesis of both enantiomers of pachastrissamine is described from a common chiral template. The stereoselective construction of the central tetrahydrofuran units was based on the pseudodesymmetrization of a pentodialdo-1,4-furanose derivative taking advantage of the latent symmetry present. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.11.048

文献信息

• Total synthesis of pachastrissamine (jaspine B) enantiomers from d-glucose
  作者：C.V. Ramana、Awadut G. Giri、Sharad B. Suryawanshi、Rajesh G. Gonnade

  DOI：10.1016/j.tetlet.2006.11.048

  日期：2007.1

  Synthesis of both enantiomers of pachastrissamine is described from a common chiral template. The stereoselective construction of the central tetrahydrofuran units was based on the pseudodesymmetrization of a pentodialdo-1,4-furanose derivative taking advantage of the latent symmetry present. (c) 2006 Published by Elsevier Ltd.