6-O-(p-acetamido)benzenesulfonyl-1,2;4.5-di-O-isopropylidene-α-D-galactopyranose | 1309857-92-8

• 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: 6-O-(p-acetamido)benzenesulfonyl-1,2;4.5-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: [(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl 4-acetamidobenzenesulfonate
• CAS: 1309857-92-8
• 化学式: C₂₀H₂₇NO₉S
• 分子量: 457.502
• InChiKey: ZZFZXMHPUNULGY-DISONHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31
• 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：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-乙酰氨基苯磺酰叠氮 、 双丙酮半乳糖 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以82%的产率得到6-O-(p-acetamido)benzenesulfonyl-1,2;4.5-di-O-isopropylidene-α-D-galactopyranose
  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

文献信息

• Reactions of several monosaccharide-derived alcohols with p-acetamidobenzenesulfonyl azide and DBU
  作者：Iulia A. Sacui、Peter Norris

  DOI：10.1016/j.tetlet.2011.03.066

  日期：2011.5

  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.