isopropyl β-L-4-azido-2,3,4-trideoxypent-2-enoglyceropyranoside | 405145-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: isopropyl β-L-4-azido-2,3,4-trideoxypent-2-enoglyceropyranoside
• 英文别名: (3R,6S)-3-azido-6-propan-2-yloxy-3,6-dihydro-2H-pyran
• CAS: 405145-93-9
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: HAAYUVMDVRCOIU-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  isopropyl β-L-4-azido-2,3,4-trideoxypent-2-enoglyceropyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到(3R,6S)-6-异丙氧基-3,6-二氢-2H-吡喃-3-胺
  参考文献：
  名称：

  Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides

  摘要：

  Starting from alkyl alpha -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl alpha -D-hex-2-enoerythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl beta -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 21a-c, azides 22a-c were exclusively obtained. and subsequently converted into the corresponding amino derivatives 23a-c. The behaviour of P-anomers 21a-c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00450-5
• 作为产物：
  描述：

  isopropyl β-D-4-O-acetyl-2,3-dideoxypent-2-enoglyceropyranoside 在 4-二甲氨基吡啶 、 Amberlite IRA-900 in azide form 、 resin IRA 900 in the methoxide form 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 6.0h， 生成 isopropyl β-L-4-azido-2,3,4-trideoxypent-2-enoglyceropyranoside
  参考文献：
  名称：

  Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides

  摘要：

  Starting from alkyl alpha -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl alpha -D-hex-2-enoerythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl beta -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 21a-c, azides 22a-c were exclusively obtained. and subsequently converted into the corresponding amino derivatives 23a-c. The behaviour of P-anomers 21a-c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00450-5

文献信息

• Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides
  作者：Cristiana Fava、Roberta Galeazzi、Giovanna Mobbili、Mario Orena

  DOI：10.1016/s0957-4166(01)00450-5

  日期：2001.10

  Starting from alkyl alpha -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl alpha -D-hex-2-enoerythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl beta -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 21a-c, azides 22a-c were exclusively obtained. and subsequently converted into the corresponding amino derivatives 23a-c. The behaviour of P-anomers 21a-c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.