2-C-(5-allylamino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)ethanol | 1092681-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-C-(5-allylamino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)ethanol
• 英文别名: (3aS,4S,7R,7aR)-4-(2-hydroxyethyl)-2,2-dimethyl-5-prop-2-enyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridin-7-ol
• CAS: 1092681-89-4
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: OMRDGLRQMOSWLR-WHOHXGKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-C-(5-allylamino-5-deoxy-2,3-di-O-isopropylidene-D-ribopyranosyl)acetate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-C-(5-allylamino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)ethanol 、 2-C-(5-allylamino-5-deoxy-2,3-di-O-isopropylidene-α-D-ribopyranosyl)ethanol
  参考文献：
  名称：

  Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides

  摘要：

  Iminoalditol analogs of ribopyranosides were prepared by reduction of a vinylogous urethane intermediate formed from methyl 2-C-(5-O-methanesulfonyl-beta-D-ribofuranosyl)acetate (1) by treatment with sodium azide in DMF at reflux. The N-alkylated analogs were synthesized either by N-alkylation of the corresponding parent iminoaldithol or, more efficiently, from the product of the reaction of 1 with various alkylamines. The latter process involves an S(N)2 substitution at C-5 by the amine followed by an intramolecular hetero-Michael reaction under basic conditions. The 'aglycon' of the iminoalditol was also modified through amidation and esterification. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.005