methyl 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetate | 1092681-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetate
• 英文别名: methyl 2-[(3aS,4S,7R,7aR)-7-hydroxy-5-[(4-methoxyphenyl)methyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridin-4-yl]acetate
• CAS: 1092681-85-0
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: SKNHIQICXMEPIK-CIRFHOKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribopyranosyl]acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以57%的产率得到2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-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
• 作为产物：
  描述：

  methyl 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-β-D-ribofuranosyl]acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以37%的产率得到methyl 2-C-[5-deoxy-2,3-di-O-isopropylidene-5-(4-methoxybenzylamino)-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

文献信息

• Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides
  作者：An-Tai Wu、Pey-Jiuann Wu、Wei Zou、Jiun-Ly Chir、Yuan-Chun Chang、Shuan-Yi Tsai、Chao-Qi Guo、Wei-Shuan Chang、Yu-Chi Hsieh

  DOI：10.1016/j.carres.2008.08.005

  日期：2008.11

  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.