methyl 2-C-(5-deoxy-2,3-di-O-isopropylidene-5-morpholinopropylamino-β-D-ribofuranosyl)acetate | 1092681-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-C-(5-deoxy-2,3-di-O-isopropylidene-5-morpholinopropylamino-β-D-ribofuranosyl)acetate
• CAS: 1092681-75-8
• 化学式: C₁₈H₃₂N₂O₆
• 分子量: 372.462
• InChiKey: GNMQTSTVEITRHN-HDEZJCGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  78.49
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2-C-(5-deoxy-2,3-di-O-isopropylidene-5-morpholinopropylamino-β-D-ribofuranosyl)acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以42%的产率得到methyl 2-C-(5-deoxy-2,3-di-O-isopropylidene-5-morpholinopropylamino-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
• 作为产物：
  描述：

  N-(3-氨丙基)吗啉 、 methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-7-O-mesyl-D-allo-heptulonate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以72%的产率得到methyl 2-C-(5-deoxy-2,3-di-O-isopropylidene-5-morpholinopropylamino-β-D-ribofuranosyl)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