4-phenylbutyl-dibenzylphosphate | 136025-58-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 4-phenylbutyl-dibenzylphosphate
• 英文别名: 4-phenylbutyldibenzyl phosphate；Dibenzyl 4-phenylbutylphosphate；Dibenzyl 4-phenylbutyl phosphate
• CAS: 136025-58-6
• 化学式: C₂₄H₂₇O₄P
• 分子量: 410.45
• InChiKey: BZIKQJFADPTQEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-phenylbutyl-dibenzylphosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到4-phenylbutylphosphoric acid
  参考文献：
  名称：

  将伯胺转化为磷酸单酯的新方法1

  摘要：

  亚硝基二苄基膦酸酯4的亚硝化能够以良好的产率由伯正烷基胺经由5合成磷酸单酯6。

  DOI：

  10.1016/s0040-4039(00)79706-1
• 作为产物：
  描述：

  亚磷酸二苄酯 在 亚硝酸异戊酯 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 4-phenylbutyl-dibenzylphosphate
  参考文献：
  名称：

  将伯胺转化为磷酸单酯的新方法1

  摘要：

  亚硝基二苄基膦酸酯4的亚硝化能够以良好的产率由伯正烷基胺经由5合成磷酸单酯6。

  DOI：

  10.1016/s0040-4039(00)79706-1

文献信息

• Exploring specificity of glycosyltransferases: synthesis of new sugar nucleotide related molecules as putative donor substrates
  作者：Amira Khaled、Olga Piotrowska、Katarzyna Dominiak、Claudine Augé

  DOI：10.1016/j.carres.2007.11.009

  日期：2008.2

  with an IC50 value of 7 mM. In the second approach, we prepared sugar nucleotide mimics having the diphosphate bridge replaced by the oxycarbonylaminosulfonyl linker. The surrogate of GDP-Fuc was synthesized as a 9:1 alpha/beta anomeric mixture, in 40% yield, starting from chlorosulfonyl isocyanate, perbenzylated l-fucopyranose, and a guanosine derivative, protected on the exocyclic amine and secondary

  我们研究了糖基转移酶在两个互补方向上对供体底物的特异性。首先，我们准备了简单的N-乙酰基-α-D-氨基葡萄糖1-二磷酸酯：甲基-（2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基）-二磷酸酯，苄基-（2-乙酰氨基-2-脱氧-α-磷酸酯D-吡喃葡萄糖基）-二磷酸酯，4-苯基丁基-（2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基）-二磷酸酯，通过将相应的活化烷基磷酸酯与N-乙酰基-α-D-葡糖胺1-偶联磷酸盐。在脑膜炎奈瑟氏菌N-乙酰氨基葡萄糖氨基转移酶（LgtA）催化的反应中，作为N-乙酰氨基葡萄糖的供体，测试了这些二磷酸以及2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖1-二磷酸的活性。评估为抑制剂，只有2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖1-二磷酸酯显示出一定的抑制活性，IC50值为7 mM。在第二种方法中，我们准备了糖核苷酸模拟物，其二磷酸桥被氧羰基氨基磺酰基接头取代。GDP-Fuc的替代
• Catalytic Lewis acid phosphorylation with pyrophosphates
  作者：Owen S. Fenton、Emily E. Allen、Kyle P. Pedretty、Sean D. Till、Joseph E. Todaro、Bianca R. Sculimbrene

  DOI：10.1016/j.tet.2012.08.070

  日期：2012.11

  We report a method for the Lewis acid catalyzed phosphorylation of alcohols with pyrophosphates. Ti((OBu)-Bu-t)(4) was found to be the most effective catalyst in the phosphorylation of both primary and secondary alcohols with tetrabenzylpyrophosphate, providing conversions between 54% and >98% and isolated yields between 50% and 97%. Other pyrophosphates with orthogonal protecting groups were synthesized and screened to validate the generality of the approach. This study will describe how benzyl, methyl, ethyl, allyl, and o-nitrobenzyl pyrophosphates are all effective phosphorylating agents under Lewis acid catalysis. (C) 2012 Elsevier Ltd. All rights reserved.
• Efficient catalyst turnover in the phosphitylation of alcohols with phosphoramidites
  作者：Patrick B. Brady、Elizabeth M. Morris、Owen S. Fenton、Bianca R. Sculimbrene

  DOI：10.1016/j.tetlet.2008.12.065

  日期：2009.3

  We report a method for catalytic phosphitylation utilizing phosphoramidites. Traditionally, this reaction is inefficient unless an excess of catalyst is present due to catalyst deactivation by an amine by-product. Isocyanate additives have been evaluated for scavenging the amine to facilitate catalyst turnover. A variety of alcohols and phosphoramidites were screened with 5 mol % catalyst. In the presence of additive, 83-97% conversion was achieved in contrast to 7-31% conversion without additive. (C) 2008 Elsevier Ltd. All rights reserved.