1,5-anhydro-6-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-α-D-gulofuranosylamine | 750586-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-6-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-α-D-gulofuranosylamine
• 英文别名: diethyl 2-[[(1S,2R,6R,7S,9R)-4,4,9-trimethyl-3,5,10-trioxa-8-azatricyclo[5.2.1.02,6]decan-8-yl]methylidene]propanedioate
• CAS: 750586-85-7
• 化学式: C₁₇H₂₅NO₇
• 分子量: 355.388
• InChiKey: AXIXLVQAHMFMDJ-WJUUCBRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  丁硫醇 、 1,5-anhydro-6-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-α-D-gulofuranosylamine 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以65%的产率得到butyl 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：

  N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-L-rhamnofuranosylamine 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77%的产率得到1,5-anhydro-6-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-α-D-gulofuranosylamine
  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.