methyl 2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosylidene)acetate | 593286-63-6

• 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-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosylidene)acetate
• CAS: 593286-63-6
• 化学式: C₁₁H₁₇NO₅
• 分子量: 243.26
• InChiKey: WOSCGJKAWKRUFX-FKTZTGRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-7-O-mesyl-D-allo-heptulonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以71%的产率得到methyl 2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribopyranosylidene)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.