(3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one | 807626-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one
• 英文别名: (3S,4S,1'S)-3-(tert-butyldimethylsilyloxy)-4-methoxycarbonyl-1-(1-phenylethyl)pyrrolidin-2-one；methyl (3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-oxo-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxylate
• CAS: 807626-26-2
• 化学式: C₂₀H₃₁NO₄Si
• 分子量: 377.556
• InChiKey: GEQXJJXGSLVSHA-XIRDDKMYSA-N

物化性质

• 沸点：
  452.2±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one 在 palladium hydroxide - carbon 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 三苯基甲烷 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 水 为溶剂， 反应 136.0h， 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 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 (3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one
  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

• WO2008/101514
  申请人：——

  公开号：——

  公开（公告）日：——
• Chiral 3-hydroxypyrrolidin-2-ones. Part 2: Stereodivergent synthesis of conformationally restricted analogues of β-homoserine
  作者：Roberta Galeazzi、Gianluca Martelli、Desiré Natali、Mario Orena、Samuele Rinaldi

  DOI：10.1016/j.tetasy.2005.03.003

  日期：2005.5

  Starting from the homochiral 3-1-butyldimethylsilyloxypyrrolidin-2-one 2, a stereodivergent synthetic route was developed leading to both 3,4-trans- and 3,4-cis-3-amino-4-hydroxymethyl pyrrolidin-2-ones, 19 and 28, that are conformationally restricted analogues of beta-homoserine 4. In addition, with a large number of 3,4-disubstituted pyrrolidin-2-ones in hand, a trend was observed for both H-3 chemical shifts and J(3,4) values, allowing the configuration to be assigned to either 3-hydroxy or 3-amino derivatives. (C) 2005 Elsevier Ltd. All rights reserved.
• 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.