(S)-Methoxy-phenyl-acetic acid (1R,2R)-2-tert-butoxycarbonylamino-1-(dimethoxy-phosphoryl)-2-phenyl-ethyl ester | 294842-91-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (S)-Methoxy-phenyl-acetic acid (1R,2R)-2-tert-butoxycarbonylamino-1-(dimethoxy-phosphoryl)-2-phenyl-ethyl ester
• CAS: 294842-91-4
• 化学式: C₂₄H₃₂NO₈P
• 分子量: 493.494
• InChiKey: PZWOJTXMDPZGRV-RZUBCFFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-Methoxy-phenyl-acetic acid (1R,2R)-2-tert-butoxycarbonylamino-1-(dimethoxy-phosphoryl)-2-phenyl-ethyl ester 在 盐酸 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 dimethyl (1R,2R)-2-(benzoylamino)-1-hydroxy-2-phenylethylphosphonate
  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：

  tert-butyl (2-oxo-1-phenylethyl)carbamate 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-Methoxy-phenyl-acetic acid (1R,2R)-2-tert-butoxycarbonylamino-1-(dimethoxy-phosphoryl)-2-phenyl-ethyl ester
  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