4-nitrophenyl 2-azido-2-deoxy-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2-azido-2-deoxy-α-D-mannopyranoside
• 英文别名: (2R,3S,4R,5S,6R)-5-azido-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4-diol
• 化学式: C₁₂H₁₄N₄O₇
• 分子量: 326.266
• InChiKey: KTWQZFHYGZLIJI-ROHXPCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  171.05
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl glucopyranose 在 sodium azide 、 sodium methylate 、 zinc(II) chloride 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 4-nitrophenyl 2-azido-2-deoxy-α-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

文献信息

• A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides
  作者：Alena Popelová、Karel Kefurt、Martina Hlaváčková、Jitka Moravcová

  DOI：10.1016/j.carres.2004.11.002

  日期：2005.1

  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.