2-deoxy-2-fluoro-3,4-di-O-benzoyl-α-1-(dibenzylphosphoryl)-L-fucopyranose | 233751-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-fluoro-3,4-di-O-benzoyl-α-1-(dibenzylphosphoryl)-L-fucopyranose
• 英文别名: (2,3-dibenzoyl-2-fluoro-α-1-fucopyranosyl) dibenzyl phosphate；[(2S,3R,4R,5S,6S)-4-benzoyloxy-6-bis(phenylmethoxy)phosphoryloxy-5-fluoro-2-methyloxan-3-yl] benzoate
• CAS: 233751-51-4
• 化学式: C₃₄H₃₂FO₉P
• 分子量: 634.595
• InChiKey: HFUFTZUPLJLOJG-AIGSBURYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-fluoro-3,4-di-O-benzoyl-α-1-(dibenzylphosphoryl)-L-fucopyranose 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

  摘要：

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00139-5
• 作为产物：
  描述：

  磷酸二苄酯 、 dibenzoyl fucal 在 1-chloromethyl-4-fluoro-1,4-diazonia-bicyclo<2.2.2>octane ditriflate 作用下， 以54%的产率得到2-deoxy-2-fluoro-3,4-di-O-benzoyl-α-1-(dibenzylphosphoryl)-L-fucopyranose
  参考文献：
  名称：

  Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

  摘要：

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00139-5

文献信息

• Electrophilic Fluorination−Nucleophilic Addition Reaction Mediated by Selectfluor: Mechanistic Studies and New Applications
  作者：Stéphane P. Vincent、Michael D. Burkart、Chung-Ying Tsai、Zhiyuan Zhang、Chi-Huey Wong

  DOI：10.1021/jo990686h

  日期：1999.7.1

  The electrophilic fluorination-nucleophilic addition reaction with Selectfluor-type reagents upon glycals has been studied and optimized. This reaction leads to selective fluorination at the 2-position with concomitant nucleophilic addition to the anomeric center. To understand the stereochemical outcome of this process, a mechanistic study has led to the discovery that, in the fucose series, Selectfluor

  已经研究和优化了与 Selectfluor 型试剂在糖基上的亲电氟化-亲核加成反应。该反应导致在 2 位选择性氟化，同时对异头中心进行亲核加成。为了了解该过程的立体化学结果，一项机制研究发现，在岩藻糖系列中，Selectfluor 以顺式方式特异性添加，产生 1-[TEDA-CH2Cl]-2-氟糖，该糖缓慢异构化为更稳定的中间体。研究了异头α/β分布作为反应物和条件的函数，发现保护基策略的明智选择可以提高氟化和亲核加成的立体选择性。此外，使用超敏自由基探针来探测反应，并且没有分离出自由基过程的产物特征，这表明在聚糖对 Selectfluor 的攻击期间没有发生单电子转移。还讨论了溶剂效应、Selectfluor 反离子和逐步程序的重要性。这项研究带来了产量的重要改进和更广泛的允许亲核试剂，如碳水化合物、氨基酸、磷酸盐或膦酸盐的仲醇。这一优化过程进一步应用于重要生物活性分子的修饰，包括氟化道
• Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases
  作者：Michael D Burkart、Stéphane P Vincent、Arno Düffels、Brion W Murray、Steven V Ley、Chi-Huey Wong

  DOI：10.1016/s0968-0896(00)00139-5

  日期：2000.8

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.