1-ethyl-4-methyl-2-tert-butyldimethylsilyloxy-3-methylenebutanedioate | 807626-23-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-ethyl-4-methyl-2-tert-butyldimethylsilyloxy-3-methylenebutanedioate
• 英文别名: 1-ethyl 4-methyl 2-(tert-butyldimethylsilyloxy)-3-methylenebutanedioate；1-O-ethyl 4-O-methyl 2-[tert-butyl(dimethyl)silyl]oxy-3-methylidenebutanedioate
• CAS: 807626-23-9
• 化学式: C₁₄H₂₆O₅Si
• 分子量: 302.443
• InChiKey: VZRAWLZWUMLHCS-UHFFFAOYSA-N

物化性质

• 沸点：
  328.2±42.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-ethyl-4-methyl-2-tert-butyldimethylsilyloxy-3-methylenebutanedioate 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯甲酸氯乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 48.17h， 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：

  叔丁基二甲基氯硅烷 、 1-Ethyl 4-methyl 2-hydroxy 3-methylenebutanedioate 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到1-ethyl-4-methyl-2-tert-butyldimethylsilyloxy-3-methylenebutanedioate
  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 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.