dimethyl (1S*,2S*)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl (1S*,2S*)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonate
• 英文别名: tert-butyl N-[(1R,2R)-2-[dimethoxy(oxido)phosphaniumyl]-2-hydroxy-1-phenylethyl]carbamate
• 化学式: C₁₅H₂₄NO₆P
• 分子量: 345.332
• InChiKey: JNMZLHDWURHJRN-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl (1S*,2S*)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonate 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (1S,2S)-2-(N-Boc-amino)-1-(dimethoxyphosphoryl)-2-phenylethyl benzoate
  参考文献：
  名称：

  Enantiomeric phosphonate analogs of the docetaxel C-13 side chain

  摘要：

  Addition of dimethyl phosphite to racemic N-Boc-phenylglycinal led to a 75:25 mixture of syn and anti dimethyl 2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonates. The syn-diastereoisomer was obtained in 50% yield after a single crystallization. Resolution of the syn-isomer was achieved via the (S)-O-methylmandelate esters. Racemization-free ammonolysis gave both enantiomers in high enantiomeric excess. Benzoates of both N-Boc syn-enantiomers were transformed into dimethyl (IR,2R)- and (1S,2S)-2-(benzoylamino)-1-hydroxy-2-phenylethylphosphonates in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00203-2
• 作为产物：
  描述：

  dimethyl (1S*,2S*)-1-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-2-phenylethylphosphonate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以65%的产率得到dimethyl (1S*,2S*)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonate
  参考文献：
  名称：

  Racemization-Free Recovery of α-Hydroxyphosphonates from Their Carboxylic Esters

  摘要：

  Ammonolysis (25% aqueous NH3 - alcohols or THF) of carboxylic esters obtained from diastereoisomerically pure alpha-hydroxyphosphonates leads to recovery of the phosphonates without racemization in good to excellent yields.

  DOI：

  10.1080/00397910008086952

文献信息

• Enantiomeric phosphonate analogs of the docetaxel C-13 side chain
  作者：Andrzej E Wróblewski、Dorota G Piotrowska

  DOI：10.1016/s0957-4166(00)00203-2

  日期：2000.6

  Addition of dimethyl phosphite to racemic N-Boc-phenylglycinal led to a 75:25 mixture of syn and anti dimethyl 2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonates. The syn-diastereoisomer was obtained in 50% yield after a single crystallization. Resolution of the syn-isomer was achieved via the (S)-O-methylmandelate esters. Racemization-free ammonolysis gave both enantiomers in high enantiomeric excess. Benzoates of both N-Boc syn-enantiomers were transformed into dimethyl (IR,2R)- and (1S,2S)-2-(benzoylamino)-1-hydroxy-2-phenylethylphosphonates in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Racemization-Free Recovery of α-Hydroxyphosphonates from Their Carboxylic Esters
  作者：Piotrowska、Halajewska-Wosik、Wroblewski

  DOI：10.1080/00397910008086952

  日期：2000.11

  Ammonolysis (25% aqueous NH3 - alcohols or THF) of carboxylic esters obtained from diastereoisomerically pure alpha-hydroxyphosphonates leads to recovery of the phosphonates without racemization in good to excellent yields.