4-nitrophenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside | 53735-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: 4-nitrophenyl 2-acetamido-2-deoxy-1-thio-β-D-glucoside；p-Nitrophenyl-2-acetamido-2-desoxy-1-thio-β-D-glucopyranosid；P-Nitrophenyl-N-acetyl-1-thio-B-D-*gluco saminide；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenyl)sulfanyloxan-3-yl]acetamide
• CAS: 53735-94-7
• 化学式: C₁₄H₁₈N₂O₇S
• 分子量: 358.372
• InChiKey: XXHJAPWYKMBYHF-KSTCHIGDSA-N

物化性质

• 沸点：
  705.1±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

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：

  4-硝基苯硫醇 、 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76%的产率得到4-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

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