N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-L-rhamnofuranosylamine | 750586-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-L-rhamnofuranosylamine
• 英文别名: diethyl 2-[[[(3aR,4S,6R,6aR)-2,2-dimethyl-6-[(1S)-1-methylsulfonyloxyethyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]amino]methylidene]propanedioate
• CAS: 750586-84-6
• 化学式: C₁₈H₂₉NO₁₀S
• 分子量: 451.495
• InChiKey: ICGQTAQEFQKONL-MQFWEAQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-L-rhamnofuranosylamine 在 sodium methylate 、 对甲苯磺酸 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 0.5h， 生成 ethyl 5,6-dideoxy-5-N-(2,2-diethoxycarbonylvinylamine)-2,3-O-isopropylidene-1-thio-α-D-gulofuranoside
  参考文献：
  名称：

  Ring contraction of glycopyranosyl enamines: an easy route to furanoid thioglycosides of 5-aminosugars

  摘要：

  The reaction of glycohexapyranosyl enamines, having 2- and 3-hydroxyl groups in a cis-relationship with 12-dimethoxypropane, induces ring contraction of the sugar ring with formation of 2,3-O-isopropylidene furanoid glycosylenamines. 5-O-Mesylation of these compounds. followed by formation of anhydroazasugars and nucleophilic ring opening, with thiols, produces alkyl and aryl thiofuranosides of 5-aminosugars. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.027
• 作为产物：
  描述：

  甲基磺酰氯 、 N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-L-rhamnofuranosylamine 在 吡啶 作用下， 反应 24.0h， 以90%的产率得到N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-L-rhamnofuranosylamine
  参考文献：
  名称：

  Ring contraction of glycopyranosyl enamines: an easy route to furanoid thioglycosides of 5-aminosugars

  摘要：

  The reaction of glycohexapyranosyl enamines, having 2- and 3-hydroxyl groups in a cis-relationship with 12-dimethoxypropane, induces ring contraction of the sugar ring with formation of 2,3-O-isopropylidene furanoid glycosylenamines. 5-O-Mesylation of these compounds. followed by formation of anhydroazasugars and nucleophilic ring opening, with thiols, produces alkyl and aryl thiofuranosides of 5-aminosugars. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.027

文献信息

• Ring contraction of glycopyranosyl enamines: an easy route to furanoid thioglycosides of 5-aminosugars
  作者：M.Ángeles Pradera、Francisco J. Sayago、José M. Illangua、Manuel Angulo、Consolación Gasch、José Fuentes

  DOI：10.1016/j.tetasy.2004.05.027

  日期：2004.7

  The reaction of glycohexapyranosyl enamines, having 2- and 3-hydroxyl groups in a cis-relationship with 12-dimethoxypropane, induces ring contraction of the sugar ring with formation of 2,3-O-isopropylidene furanoid glycosylenamines. 5-O-Mesylation of these compounds. followed by formation of anhydroazasugars and nucleophilic ring opening, with thiols, produces alkyl and aryl thiofuranosides of 5-aminosugars. (C) 2004 Elsevier Ltd. All rights reserved.