2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-4-O-mesyl-β-L-rhamnopyranosylamine | 678142-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-4-O-mesyl-β-L-rhamnopyranosylamine
• 英文别名: diethyl 2-[[[(2S,3R,4S,5S,6S)-3,4-dibenzoyloxy-6-methyl-5-methylsulfonyloxyoxan-2-yl]amino]methylidene]propanedioate
• CAS: 678142-33-1
• 化学式: C₂₉H₃₃NO₁₂S
• 分子量: 619.647
• InChiKey: WEGSLRREFRDEHO-JIKCRDEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-4-O-mesyl-β-L-rhamnopyranosylamine 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、2.67 kPa 条件下， 反应 0.25h， 以60%的产率得到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-di(ethoxycarbonyl)vinyl)-2,3-O-(4-methoxybenzylidene)-β-L-rhamnopyranosylamine 在 吡啶 、 对甲苯磺酸 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-4-O-mesyl-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.