(2S,3R)-methyl 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionate | 815620-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3R)-methyl 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionate
• 英文别名: methyl 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropanoate；methyl (2S,3R)-3-hydroxy-2-(4-methoxyphenoxy)-3-phenylpropanoate
• CAS: 815620-36-1
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: RSWILLTYYBFERY-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-methyl 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionate 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 [(1R,2S)-2-hydroxy-3-methoxy-3-oxo-1-phenylpropyl] benzoate
  参考文献：
  名称：

  Oxadiazinones as chiral auxiliaries: increased diastereoselectivities in the glycolate aldol reaction of oxadiazinones

  摘要：

  Glycolate aldol reactions were conducted using a (1R,2S)-norephedrine based N-4-isopropyloxadiazinone as a chiral template to afford aldol adducts 8a-h. The yields ranged from 57% to 99% while the diastereoselectivities ranged from 94:6 to 99:1. Adduct 8a was hydrolyzed to afford the oxadiazinone auxiliary and P-hydroxyacid 9, which was converted to the known methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate 12 with 95% ee as determined by chiral HPLC. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.015
• 作为产物：
  描述：

  (5S,6R)-3,4,5,6,-tetrahydro-4-isopropyl-[2-(p-methoxyphenoxy)acetyl]-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one 在 sodium hydroxide 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 生成 (2S,3R)-methyl 3-hydroxy-2-(p-methoxyphenoxy)-3-phenylpropionate
  参考文献：
  名称：

  Oxadiazinones as chiral auxiliaries: increased diastereoselectivities in the glycolate aldol reaction of oxadiazinones

  摘要：

  Glycolate aldol reactions were conducted using a (1R,2S)-norephedrine based N-4-isopropyloxadiazinone as a chiral template to afford aldol adducts 8a-h. The yields ranged from 57% to 99% while the diastereoselectivities ranged from 94:6 to 99:1. Adduct 8a was hydrolyzed to afford the oxadiazinone auxiliary and P-hydroxyacid 9, which was converted to the known methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate 12 with 95% ee as determined by chiral HPLC. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.015

文献信息

• syn-Diastereoselective glycolate aldol addition reactions of an N(3)-(p-methoxyphenoxy)acetyloxazolidine-2-thione
  作者：Craig S. Haynes、Cassie A. Goodman、Juandah Bruce、Sarah C. Genin、Brad J. Austermuehle、Victor L. Leong、Austin R. Leise、Robert Larson、Christopher G. Hamaker、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2016.11.001

  日期：2017.1

  An N-3-(p-methoxyphenoxy)acetyloxazolidine-2-thione has been synthesized and employed in glycolate asymmetric aldol addition reactions with aromatic and aliphatic aldehydes. It was determined that the titanium tetrachloride medicated aldol reaction afforded diastereoselectivities that ranged from 75:25 to 94:6 when the reaction was conducted at -78 degrees C. The absolute stereochemistry of the aldol adducts was determined by H-1 NMR spectroscopy and X-ray crystallography. The H-1 NMR spectra of the aldol adducts contained a signal (the a-proton of the glycolate position of the aldol side chain) that was highly deshielded due to conformational restriction about the N(3)-(p-methoxyphenoxy)acetyl side chain and the oxazolidine-2-thione auxiliary. (C) 2016 Elsevier Ltd. All rights reserved.