benzyl (4S)-4-(dibenzylamino)-6-dimethoxyphosphoryl-5-oxohexanoate | 1114400-86-0

• 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: benzyl (4S)-4-(dibenzylamino)-6-dimethoxyphosphoryl-5-oxohexanoate
• CAS: 1114400-86-0
• 化学式: C₂₉H₃₄NO₆P
• 分子量: 523.566
• InChiKey: PHLOKJXKEJLBPP-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  dibenzyl N,N-dibenzyl-L-glutamate 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.67h， 以65%的产率得到(S)-2-dibenzylamino-6-(dimethoxy-phosphoryl)-5-oxohexanoicacid benzyl ester
  参考文献：
  名称：

  Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine

  摘要：

  (S)-2-Amino-4-(2-pentadecyl-1,3-dioxolan-2-yl)-butanoic acid, 11, Pdiob, a synthetic analogue C-isostere of palmitoylated cysteine, has been prepared starting from tetrabenzyl glutamic acid. The less hindered benzyl carboxylate ester was transformed into the corresponding beta-ketophosphonate and subjected to a Horner-Wadsworth-Emmons reaction followed by hydrogenation/hydrogenolysis. This product was used for the preparation on solid phase and under microwave dielectric heating of a highly lipidated peptide that can be considered as an acid stable analogue of the C-terminus of the H-Ras heptapeptides 180-186. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.033

文献信息

• Transformation of Glutamic Acid into (<i>S</i>)-Benzyl 2-(dibenzylamino)-6-(dimethoxyphosphoryl)-5-oxohexanoate for a Convenient Access to 5-Substituted Prolines
  作者：Maurizio Taddei、Elena Cini、Gianluca Giorgi、Manuela Rodriquez

  DOI：10.1055/s-0029-1217340

  日期：——

  l-Glutamic acid was transformed into β-keto-phosphonate in two steps. This compound was employed in the stereocontrolled synthesis of cis-5-substituted prolines through a Woodward-Horner-Emmons (WHE) reaction with different aldehydes followed by hydrogenolysis/hydrogenation-mediated ring closure. We found also that a one-pot sequential hydroformylation-WHE reaction was possible with cis-5-substituted prolines. In addition to differently functionalised prolines, an indolizidine amino acid with a structure related to constrained peptidomimetics was obtained.

  L-谷氨酸分两步转化为β-酮膦酸盐。该化合物通过与不同醛的伍德沃德-霍纳-埃蒙斯 (WHE) 反应，然后进行氢解/氢化介导的闭环，用于顺式 5-取代脯氨酸的立体控制合成。我们还发现，顺式 5-取代的脯氨酸可以进行一锅连续加氢甲酰化-WHE 反应。除了不同功能化的脯氨酸之外，还获得了具有与受限肽模拟物相关的结构的吲哚里西啶氨基酸。