(1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine | 610314-52-8

• 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: (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine
• 英文别名: diethyl 2-[(1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-5-ethylsulfanyl-1-[(4-methoxyphenyl)methoxymethyl]-1,3,5,6,7,7a-hexahydropyrrolo[1,2-c][1,3]oxazol-3-yl]propanedioate
• CAS: 610314-52-8
• 化学式: C₃₈H₄₃NO₁₁S
• 分子量: 721.826
• InChiKey: SGMHUIHJGNOLCM-WJZCPKBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  51
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(1S,3S,5S,6R,7S,7aS)-3-di(ethoxycarbonyl)methyl-5-ethylthio-6,7-dihydroxy-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine
  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-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 在 吡啶 、 3 A molecular sieve 、 sodium methylate 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、2.67 kPa 条件下， 反应 76.0h， 生成 (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine
  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.