2,3,4-tri-O-(m-methylbenzoyl)-β-D-xylopyranosyl fluoride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-tri-O-(m-methylbenzoyl)-β-D-xylopyranosyl fluoride
• 英文别名: 2,3,4-tri-O-m-methylbenzoyl-D-xylopyranosyl fluoride；[(3R,4S,5R,6S)-6-fluoro-4,5-bis[(3-methylbenzoyl)oxy]oxan-3-yl] 3-methylbenzoate
• 化学式: C₂₉H₂₇FO₇
• 分子量: 506.528
• InChiKey: QNJAZUGMOBQGEI-XDZVQPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  D-吡喃木糖 、 N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 在 N,N-二乙基-alpha,alpha-二氟-3-甲基苄胺 作用下， 反应 12.0h， 以60%的产率得到2,3,4-tri-O-(m-methylbenzoyl)-β-D-xylopyranosyl fluoride
  参考文献：
  名称：

  Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro-(m-methylbenzyl)amine

  摘要：

  Deoxyfluorination of alcohols was carried out using N,N-diethyl-alpha,alpha-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.089

文献信息

• Selective synthesis of fluorinated carbohydrates using N , N -diethyl-α,α-difluoro-( m -methylbenzyl)amine
  作者：Shingo Kobayashi、Atushi Yoneda、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1016/j.tetlet.2003.11.121

  日期：2004.2

  Deoxyfluorination of a hydroxy group in carbohydrates was carried out using N,N-diethyl-alpha,alpha-difluoro-(m-methylbenzyl)amine. A primary hydroxy group in carbohydrates was effectively converted to the corresponding fluoride under microwave irradiation or at 100degreesC. Deoxyfluorination of hydroxy groups at the anomeric position proceeded at below room temperature, and glycosyl fluorides Could be obtained in good yields. The reaction chemoselectively proceeded, and various protecting groups of carbohydrates can survive under the reaction conditions. (C) 2003 Elsevier Ltd. All rights reserved.
• Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro-(m-methylbenzyl)amine
  作者：Shingo Kobayashi、Atushi Yoneda、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1016/j.tet.2004.05.089

  日期：2004.8

  Deoxyfluorination of alcohols was carried out using N,N-diethyl-alpha,alpha-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.