propargyl 2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)acetate | 1092681-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propargyl 2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)acetate
• 英文别名: prop-2-ynyl 2-[(3aS,4S,7R,7aR)-7-hydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-4-yl]acetate
• CAS: 1092681-79-2
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: ZNZFXXXTAGTQJH-BSJXLVFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  propargyl 2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)acetate 、 methyl 3,6-anhydro-7-azido-2,7-dideoxy-4,5-O-isopropylidene-D-allo-heptulonate 在 铜 、 copper(II) sulfate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以47%的产率得到[1-[[(3aR,4R,6S,6aS)-6-(2-methoxy-2-oxoethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl]triazol-4-yl]methyl 2-[(3aS,4S,7R,7aR)-7-hydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-4-yl]acetate
  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
• 作为产物：
  描述：

  2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)acetic acid 、 2-丙炔-1-醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到propargyl 2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosyl)acetate
  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