4-nitrophenyl 3,4,6-tri-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside | 845271-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 3,4,6-tri-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside
• CAS: 845271-56-9
• 化学式: C₁₉H₂₀F₃NO₁₃S
• 分子量: 559.428
• InChiKey: QOKHADQTQWSKEJ-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  183.87
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 3,4,6-tri-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside 在 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.33h， 生成 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside
  参考文献：
  名称：

  A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides

  摘要：

  4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta1-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20 % and 44 % overall yields, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.002
• 作为产物：
  描述：

  bromure de tri-O-acetyl-3,4,6-α-D-glucopyranosyle 在 potassium carbonate 作用下， 以 吡啶 、 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 4-nitrophenyl 3,4,6-tri-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside
  参考文献：
  名称：

  A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides

  摘要：

  4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta1-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20 % and 44 % overall yields, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.002