N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine | 678142-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine
• 英文别名: diethyl 2-[[[(3aR,4S,6S,7S,7aR)-7-hydroxy-2-(4-methoxyphenyl)-6-methyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]amino]methylidene]propanedioate
• CAS: 678142-31-9
• 化学式: C₂₂H₂₉NO₉
• 分子量: 451.474
• InChiKey: XTEBFGYRJHDXRU-NNLDNWRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine 在 吡啶 、 sodium methylate 、 对甲苯磺酸 、 乙硫醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、2.67 kPa 条件下， 反应 52.25h， 生成 1,4-anhydro-2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-β-L-rhamnopyranosylamine
  参考文献：
  名称：

  Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides

  摘要：

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.003
• 作为产物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine 、 4-甲氧基苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、2.67 kPa 条件下， 反应 25.0h， 以98%的产率得到N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine
  参考文献：
  名称：

  Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides

  摘要：

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.003

文献信息

• Anhydroazasugars as key intermediates in the stereocontrolled preparation of azasugars and their ethyl thioglycosides
  作者：José Fuentes、Francisco J. Sayago、José M. Illangua、Consolación Gasch、Manuel Angulo、M. Ángeles Pradera

  DOI：10.1016/j.tetasy.2004.01.003

  日期：2004.2

  Bicyclic azasugar thioglycosides, a new type of azasugar and alkaloid derivative, are stereo selectively prepared from easily available glycosylenamines (D-gluco and L-rhamno configurations), via 1,4-anhydroazasugar derivatives. Polyhydroxylated pyrrolidines (nonreducing pyrrolidine azasugars) are also prepared by reduction with sodium cyanoborohydride of the same 1,4-anhydroazasugars. The stereochemical assignments of the new stereogenic centres are based on NMR experiments, including a study of the interproton distances from quantitative treatment of NOE data and molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.