methyl (3S)-3-[(S)-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-hydroxymethyl]-4-oxo-4-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butanoate | 1428741-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (3S)-3-[(S)-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-hydroxymethyl]-4-oxo-4-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butanoate
• CAS: 1428741-15-4
• 化学式: C₂₅H₃₉NO₈Si
• 分子量: 509.672
• InChiKey: OOUZTFIRRKNXEA-NJNPRVFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (3S)-3-[(S)-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-hydroxymethyl]-4-oxo-4-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butanoate 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 dimethyl sulfide borane 、 双氧水 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 42.25h， 生成 (3R,4R)-4-((S)-(tert-butyldimethylsilyloxy)(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)methyl)-3-(4-(tert-butyldimethylsilyloxy)-3-methoxybenzyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric aldol approach to dibenzylbutyrolactone lignans: synthesis of (−)-(7′S)-hydroxymatairesinol and (−)-(7′S)-hydroxyarctigenin

  摘要：

  A competent and general asymmetric synthesis of 7'-hydroxydibenzylbutyrolactone lignans such as (7'S)-hydroxymatairesinol and (7'S)-hydroxyarctigenin has been reported from N-succinyl-2-oxazolidinone in six steps where diastereoselective aldol reaction and stereoselective alkylation serve as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.044
• 作为产物：
  描述：

  methyl 4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate 、 O-tert-butyldimethylsilylvanillin 在 双环己基(三氟甲烷磺酰氧基)硼烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到
  参考文献：
  名称：

  Asymmetric aldol approach to dibenzylbutyrolactone lignans: synthesis of (−)-(7′S)-hydroxymatairesinol and (−)-(7′S)-hydroxyarctigenin

  摘要：

  A competent and general asymmetric synthesis of 7'-hydroxydibenzylbutyrolactone lignans such as (7'S)-hydroxymatairesinol and (7'S)-hydroxyarctigenin has been reported from N-succinyl-2-oxazolidinone in six steps where diastereoselective aldol reaction and stereoselective alkylation serve as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.044

文献信息

• Asymmetric aldol approach to dibenzylbutyrolactone lignans: synthesis of (−)-(7′S)-hydroxymatairesinol and (−)-(7′S)-hydroxyarctigenin
  作者：Saumen Hajra、Abhisek Mandal、Sunit Hazra

  DOI：10.1016/j.tetlet.2013.02.044

  日期：2013.4

  A competent and general asymmetric synthesis of 7'-hydroxydibenzylbutyrolactone lignans such as (7'S)-hydroxymatairesinol and (7'S)-hydroxyarctigenin has been reported from N-succinyl-2-oxazolidinone in six steps where diastereoselective aldol reaction and stereoselective alkylation serve as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.