dimethyl (R)-(+)-3-(N-benzyl-N-α-methylbenzyl)-amino-2-oxopropylphosphonate

• 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: dimethyl (R)-(+)-3-(N-benzyl-N-α-methylbenzyl)-amino-2-oxopropylphosphonate
• 英文别名: 1-[benzyl-[(1R)-1-phenylethyl]amino]-3-[dimethoxy(oxido)phosphaniumyl]propan-2-one
• 化学式: C₂₀H₂₆NO₄P
• 分子量: 375.404
• InChiKey: KBHMYOIYGVGJCZ-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (R)-(+)-3-(N-benzyl-N-α-methylbenzyl)-amino-2-oxopropylphosphonate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 {(S)-3-[Benzyl-((R)-1-phenyl-ethyl)-amino]-2-hydroxy-propyl}-phosphonic acid dimethyl ester 、 {(R)-3-[Benzyl-((R)-1-phenyl-ethyl)-amino]-2-hydroxy-propyl}-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Highly diastereoselective reduction of β-ketophosphonates bearing homochiral bis(α-methylbenzyl)amine: preparation of both enantiomers of phosphogabob (GABOBP)

  摘要：

  The reduction of dimethyl 3-N,N-di(alpha-methylbenzyl)amino-2-ketophosphonates 9 with catecholborane at -78degreesC in presence of LiClO4, gave gamma-amino-beta-hydroxyphosphonates 10 and 11 in good yield and with excellent diastereoselectivity. This procedure represents an example of highly diastereoselective 1,4-induction. The hydrolysis and hydrogenation of 10 and 11 afforded the (R)- and (S)-gamma-amino-beta-hydroxypropylphosphonic acid (GABOB(P)), respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.033
• 作为产物：
  描述：

  甲基膦酸二甲酯 、 ethyl (R)-(+)-(N-benzyl-N-α-methylbenzyl)glycinate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 以85%的产率得到dimethyl (R)-(+)-3-(N-benzyl-N-α-methylbenzyl)-amino-2-oxopropylphosphonate
  参考文献：
  名称：

  Highly diastereoselective reduction of β-ketophosphonates bearing homochiral bis(α-methylbenzyl)amine: preparation of both enantiomers of phosphogabob (GABOBP)

  摘要：

  The reduction of dimethyl 3-N,N-di(alpha-methylbenzyl)amino-2-ketophosphonates 9 with catecholborane at -78degreesC in presence of LiClO4, gave gamma-amino-beta-hydroxyphosphonates 10 and 11 in good yield and with excellent diastereoselectivity. This procedure represents an example of highly diastereoselective 1,4-induction. The hydrolysis and hydrogenation of 10 and 11 afforded the (R)- and (S)-gamma-amino-beta-hydroxypropylphosphonic acid (GABOB(P)), respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.033

文献信息

• Highly diastereoselective reduction of β-ketophosphonates bearing homochiral bis(α-methylbenzyl)amine: preparation of both enantiomers of phosphogabob (GABOBP)
  作者：Mario Ordóñez、Angelina González-Morales、Humberto Salazar-Fernández

  DOI：10.1016/j.tetasy.2004.07.033

  日期：2004.9

  The reduction of dimethyl 3-N,N-di(alpha-methylbenzyl)amino-2-ketophosphonates 9 with catecholborane at -78degreesC in presence of LiClO4, gave gamma-amino-beta-hydroxyphosphonates 10 and 11 in good yield and with excellent diastereoselectivity. This procedure represents an example of highly diastereoselective 1,4-induction. The hydrolysis and hydrogenation of 10 and 11 afforded the (R)- and (S)-gamma-amino-beta-hydroxypropylphosphonic acid (GABOB(P)), respectively. (C) 2004 Elsevier Ltd. All rights reserved.