1,4-anhydro-2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-β-L-rhamnopyranosylamine | 610314-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-anhydro-2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-β-L-rhamnopyranosylamine
• 英文别名: diethyl 2-[[(1S,3S,4R,5R,6R)-5,6-dibenzoyloxy-3-methyl-2-oxa-7-azabicyclo[2.2.1]heptan-7-yl]methylidene]propanedioate
• CAS: 610314-57-3
• 化学式: C₂₈H₂₉NO₉
• 分子量: 523.54
• InChiKey: HSGLKHGPWRRRHJ-QNBQWMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-β-L-rhamnopyranosylamine 在 sodium methylate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 (2R,3R,4S,1'S)-1-acetyl-3,4-dihydroxy-2-(1'-hydroxyethyl)pyrrolidine
  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-di(ethoxycarbonyl)vinyl)-4-O-mesyl-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 28.25h， 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

文献信息

• Stereoselective synthesis of azasugar thioglycosides
  作者：M.Angeles Pradera、Francisco J. Sayago、José M. Illangua、Consolación Gasch、José Fuentes

  DOI：10.1016/s0040-4039(03)01685-x

  日期：2003.8

  Bicyclic (2-oxapyrrolizidines) and monocyclic (piperidine) azasugar ethyl thioglycosides, a new type of azasugar derivative, are stereoselectively prepared from suitable glycosylenamines, through anhydroazasugar derivatives. (C) 2003 Elsevier Ltd. All rights reserved.