2-(tert-butoxycarbonyl)amino-2-ethyl-3-hydroxylpropyl dibenzyl phosphate | 1401995-59-2

• 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: 2-(tert-butoxycarbonyl)amino-2-ethyl-3-hydroxylpropyl dibenzyl phosphate
• 英文别名: 2-(tert-butoxycarbonyl)amino-2-ethyl-3-hydroxylpropyldibenzyl phosphate；2-(tert-butoxycarbonyl)amino-2-ethyl-3-hydroxypropyl dibenzyl phosphate；tert-butyl N-[1-bis(phenylmethoxy)phosphoryloxy-2-(hydroxymethyl)butan-2-yl]carbamate
• CAS: 1401995-59-2
• 化学式: C₂₄H₃₄NO₇P
• 分子量: 479.51
• InChiKey: WWXUCPDOBSEAQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基-2-丙基[1-羟基-2-(羟基甲基)-2-丁烷基]氨基甲酸酯 、 焦磷酸四苄酯 在 titanium(IV) tetrabutoxide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以93%的产率得到2-(tert-butoxycarbonyl)amino-2-ethyl-3-hydroxylpropyl dibenzyl phosphate
  参考文献：
  名称：

  Catalytic Lewis acid phosphorylation with pyrophosphates

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.08.070

文献信息

• Selective phosphorylation of diols with a Lewis acid catalyst
  作者：Kyle A. Coppola、Joseph W. Testa、Emily E. Allen、Bianca R. Sculimbrene

  DOI：10.1016/j.tetlet.2014.05.047

  日期：2014.7

  We report a method for the Lewis acid catalyzed phosphorylation of dials with pyrophosphates. Titanium alkoxides were found to be effective catalysts in the selective mono-phosphorylation for a range of dials. Dials of varying chain lengths and substituents were screened, to study the factors that influence mono-versus di-phosphorylation. It was discovered that 2-alkyl-2-amino-1,3-propanediols can be selectively mono-phosphoiylated in up to 97% isolated yield. This structural core is mono-phosphorylated in numerous immunomodulating compounds including the FDA-approved drug, FTY720.[GRAPHICS](C) 2014 Elsevier Ltd. All rights reserved.