1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose | 177562-09-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose
• 英文别名: 2,3;5,6-Di-O-isopropylidene-1-O-(2-phenylacetyl)-alpha-D-mannofuranose；[(3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl] 2-phenylacetate
• CAS: 177562-09-3
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: NXWTYFHFSHYVAL-MWIANEHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 1-O-(2-diazo-2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose 、 1-azido-1-deoxy-2,3:5,6-di-O-isopropylidene-β-D-mannofuranose 、 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose
  参考文献：
  名称：

  Reactions of several monosaccharide-derived alcohols with p-acetamidobenzenesulfonyl azide and DBU

  摘要：

  Attempted diazo transfer to 1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-alpha-D-mannofuranose using p-acetamidobenzenesulfonyl azide (p-ABSA) and DBU as base affords 1-O-(2-diazo-2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-alpha-D-mannofuranose in low yield along with 2,3;5.6-di-O-isopropylidene-alpha-D-mannofuranose. 1-azido-2,3;5,6-di-O-isopropylidene-beta-D-mannofuranose, as well as the unreacted starting material. The azido sugar likely arises from alpha-mannofuranosyl sulfonate ester formation, through displacement of azide from p-ABSA by the sugar lactol, followed by stereospecific displacement by azide anion on the furanosyl sulfonate ester. This outcome has been studied further with the conditions being applied to several common monosaccharide derivatives. Accessible substrates afford the azido sugar in an overall one-pot alcohol-to-azide conversion, while hindered substrates yield the sulfonate esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.066
• 作为产物：
  描述：

  苯乙酸 、 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 以90%的产率得到1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose
  参考文献：
  名称：

  Reactions of several monosaccharide-derived alcohols with p-acetamidobenzenesulfonyl azide and DBU

  摘要：

  Attempted diazo transfer to 1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-alpha-D-mannofuranose using p-acetamidobenzenesulfonyl azide (p-ABSA) and DBU as base affords 1-O-(2-diazo-2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-alpha-D-mannofuranose in low yield along with 2,3;5.6-di-O-isopropylidene-alpha-D-mannofuranose. 1-azido-2,3;5,6-di-O-isopropylidene-beta-D-mannofuranose, as well as the unreacted starting material. The azido sugar likely arises from alpha-mannofuranosyl sulfonate ester formation, through displacement of azide from p-ABSA by the sugar lactol, followed by stereospecific displacement by azide anion on the furanosyl sulfonate ester. This outcome has been studied further with the conditions being applied to several common monosaccharide derivatives. Accessible substrates afford the azido sugar in an overall one-pot alcohol-to-azide conversion, while hindered substrates yield the sulfonate esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.066