2-chloro-4-nitrophenyl 3,4-di-O-tert-butyldimethylsilyl-β-L-fucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-4-nitrophenyl 3,4-di-O-tert-butyldimethylsilyl-β-L-fucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(2-chloro-4-nitrophenoxy)-6-methyloxan-3-ol
• 化学式: C₂₄H₄₂ClNO₇Si₂
• 分子量: 548.224
• InChiKey: DPLNALDZZQJIDQ-JHAAVKQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-碘代丁二酰亚胺 、 2-氯-4-硝基苯酚 、 ethyl 3,4-di-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以61%的产率得到2-chloro-4-nitrophenyl 3,4-di-O-tert-butyldimethylsilyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of 2-chloro-4-nitrophenyl α-l-fucopyranoside: a substrate for α-l-fucosidase (AFU)

  摘要：

  An effective method to prepare the substrate of alpha-L-fucosidase (AFU) is described. Ethyl 1-thiofucoside with a free 2-OH group was used as the glycosyl donor, and there was found no self-condensed side product. The use of the HF . pyridine reagent to remove the silyl protecting group in the last step afforded a target molecule of high purity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00244-1

文献信息

• Synthesis of 2-chloro-4-nitrophenyl α-l-fucopyranoside: a substrate for α-l-fucosidase (AFU)
  作者：Guofeng Gu、Yuguo Du、Hongyan Hu、Cheng Jin

  DOI：10.1016/s0008-6215(03)00244-1

  日期：2003.7

  An effective method to prepare the substrate of alpha-L-fucosidase (AFU) is described. Ethyl 1-thiofucoside with a free 2-OH group was used as the glycosyl donor, and there was found no self-condensed side product. The use of the HF . pyridine reagent to remove the silyl protecting group in the last step afforded a target molecule of high purity. (C) 2003 Elsevier Ltd. All rights reserved.