2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-4-O-mesyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosylamine | 678142-27-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-4-O-mesyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosylamine
• 英文别名: diethyl 2-[[[(2R,3R,4R,5R,6R)-3,4-dibenzoyloxy-6-[(4-methoxyphenyl)methoxymethyl]-5-methylsulfonyloxyoxan-2-yl]amino]methylidene]propanedioate
• CAS: 678142-27-3
• 化学式: C₃₇H₄₁NO₁₄S
• 分子量: 755.797
• InChiKey: ZMZBLTCXFUONKG-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  197
• 氢给体数：
  1
• 氢受体数：
  15

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-6-O-(4-methoxybenzyl)-β-D-glucopyranosylamine 在 sodium methylate 、 sodium cyanoborohydride 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 [(3S,4S,5S)-1-acetyl-4-benzoyloxy-5-[(1S)-1-hydroxy-2-[(4-methoxyphenyl)methoxy]ethyl]pyrrolidin-3-yl] benzoate
  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-D-glucopyranosylamine 在 吡啶 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、2.67 kPa 条件下， 反应 75.5h， 生成 2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-4-O-mesyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosylamine
  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.