2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetic acid | 1092681-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetic acid
• CAS: 1092681-82-7
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: FIMNTCYJYPLUTN-HDEZJCGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  88.46
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetic acid 、 丙烯胺 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以62%的产率得到N-allyl 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetamide
  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：

  methyl 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以82%的产率得到2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetic acid
  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