1,4-anhydro-N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine | 610314-55-1

• 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: 1,4-anhydro-N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine
• 英文别名: diethyl 2-[[(1R,2R,6R,7S,9S)-4-(4-methoxyphenyl)-9-methyl-3,5,8-trioxa-10-azatricyclo[5.2.1.02,6]decan-10-yl]methylidene]propanedioate
• CAS: 610314-55-1
• 化学式: C₂₂H₂₇NO₈
• 分子量: 433.458
• InChiKey: NBSCZPIJLWSAQO-XPCZANJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙硫醇 、 1,4-anhydro-N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以60%的产率得到2-((1S,3R,6R,7R,7aS)-5-Ethylsulfanyl-6,7-dihydroxy-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-yl)-malonic acid diethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of azasugar thioglycosides

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(03)01685-x
• 作为产物：
  描述：

  N-(2,2-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine 在 吡啶 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、2.67 kPa 条件下， 反应 24.25h， 生成 1,4-anhydro-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

• 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.
• 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.