(3R,4R,1'S)-4-benzyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidine | 807626-35-3

• 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: (3R,4R,1'S)-4-benzyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidine
• CAS: 807626-35-3
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: VLIPPNLRBUFUEC-DBVUQKKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,1'S)-4-benzyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidine 在 palladium hydroxide - carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine
  参考文献：
  名称：

  Chiral 3-hydroxypyrrolidin-2-ones from a Baylis–Hillman adduct: convergent, stereoselective synthesis of a glycosidase inhibitor

  摘要：

  The O-silyl derivative 4b, prepared starting from the Baylis-Hillman adduct 4a, underwent cyclization on treatment with (S)-phenylethylamine, to give to an equimolar mixture of the 4,5-cis-disubstituted pyrrolidin-2-ones 9 and 10, exclusively, which after separation by silica gel chromatography were both converted into the 3-hydroxy-4-hydroxymethylpyrrolidine 1 a glycosidase inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.016
• 作为产物：
  描述：

  1-Ethyl 4-methyl 2-hydroxy 3-methylenebutanedioate 在 咪唑 、 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 三苯基甲烷 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 (3R,4R,1'S)-4-benzyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidine
  参考文献：
  名称：

  Chiral 3-hydroxypyrrolidin-2-ones from a Baylis–Hillman adduct: convergent, stereoselective synthesis of a glycosidase inhibitor

  摘要：

  The O-silyl derivative 4b, prepared starting from the Baylis-Hillman adduct 4a, underwent cyclization on treatment with (S)-phenylethylamine, to give to an equimolar mixture of the 4,5-cis-disubstituted pyrrolidin-2-ones 9 and 10, exclusively, which after separation by silica gel chromatography were both converted into the 3-hydroxy-4-hydroxymethylpyrrolidine 1 a glycosidase inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.016

文献信息

• Chiral 3-hydroxypyrrolidin-2-ones from a Baylis–Hillman adduct: convergent, stereoselective synthesis of a glycosidase inhibitor
  作者：Roberta Galeazzi、Gianluca Martelli、Giovanna Mobbili、Mario Orena、Samuele Rinaldi

  DOI：10.1016/j.tetasy.2004.08.016

  日期：2004.10

  The O-silyl derivative 4b, prepared starting from the Baylis-Hillman adduct 4a, underwent cyclization on treatment with (S)-phenylethylamine, to give to an equimolar mixture of the 4,5-cis-disubstituted pyrrolidin-2-ones 9 and 10, exclusively, which after separation by silica gel chromatography were both converted into the 3-hydroxy-4-hydroxymethylpyrrolidine 1 a glycosidase inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.