2-nitrophenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-nitrophenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(2-nitrophenyl)sulfanyloxan-3-yl]acetamide
• 化学式: C₁₄H₁₈N₂O₇S
• 分子量: 358.372
• InChiKey: ACLGDEYSPAQUPT-FZGMBXNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  邻硝基苯硫酚 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以69%的产率得到2-nitrophenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and aryl thiols or disulfides

  摘要：

  An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis conditions. This simple procedure compresses up to three synthetic steps into a one-pot reaction, obviating the need for tedious workups and chromatography and directly furnishes crystalline materials in good yields. The procedure is compatible with a range of thiols and disulfides and may be amenable for preparing a wide range of thioglycosides with various glycons and aglycons. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.12.009

文献信息

• A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and aryl thiols or disulfides
  作者：Keith A. Stubbs、Matthew S. Macauley、David J. Vocadlo

  DOI：10.1016/j.carres.2005.12.009

  日期：2006.7

  An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis conditions. This simple procedure compresses up to three synthetic steps into a one-pot reaction, obviating the need for tedious workups and chromatography and directly furnishes crystalline materials in good yields. The procedure is compatible with a range of thiols and disulfides and may be amenable for preparing a wide range of thioglycosides with various glycons and aglycons. (c) 2006 Elsevier Ltd. All rights reserved.