diethyl (2S,3S)-3-bromo-2-trimethylsilyloxysuccinate | 157161-96-1

• 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: diethyl (2S,3S)-3-bromo-2-trimethylsilyloxysuccinate
• 英文别名: Diethyl (2S,3S)-2-bromo-3-(trimethylsiloxy)succinate；diethyl (2S,3S)-2-bromo-3-trimethylsilyloxybutanedioate
• CAS: 157161-96-1
• 化学式: C₁₁H₂₁BrO₅Si
• 分子量: 341.274
• InChiKey: YRSRHJBSVCMTKH-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  diethyl (2S,3S)-3-bromo-2-trimethylsilyloxysuccinate 以62%的产率得到
  参考文献：
  名称：

  Nagano Hajimo, Kuno Yukie, J. Chem. Soc. Chem. Commun, (1994) N 8, S 987-988

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 二乙基(2S,3S)-2-溴-3-羟基琥珀酸盐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到diethyl (2S,3S)-3-bromo-2-trimethylsilyloxysuccinate
  参考文献：
  名称：

  Stereocontrol in radical-mediated allylation of acyclic α-bromo-β-siloxy esters by complexation with lanthanide shift reagents Ln(fod)₃

  摘要：

  Stereoselectivity in the radical-mediated allylation of alpha-bromo-beta-siloxy esters 2 yielding alpha-allyl-beta-siloxy esters 3 (syn) and 4 (anti) was remarkably affected when the reaction was conducted in the presence of Ln(fod)(3) [= tris-(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyloctane-3,5-dionato)lanthanide]. In the allylation of alpha-bromo-beta-siloxysuccinate esters 2c and 2d affording preferentially syn-diastereoisomers 3c and 3d through chelated transition states a stoichiometric amount of the Lewis acid [Eu(fod)(3) or La(fod)(3)] was required in order to maximize the stereoselectivities, whereas in the reaction of alpha-bromo-beta-siloxybutanoate esters 2g and 2h and alpha-bromo-beta-siloxy-beta-phenylpropanoate ester 2i the effect induced by the coordination of Eu(fod)(3) to the ester group was catalytic.

  DOI：

  10.1039/p19960000389

文献信息

• 1,2-Asymmetric induction in radical-mediated allylation of diethyl (2S,3S)-3-bromo-2-oxysuccinates: efficient stereoselectivity enhancement by complexation with Eu(fod)3
  作者：Hajime Nagano、Yukie Kuno

  DOI：10.1039/c39940000987

  日期：——

  Allylation of diethyl (2S, 3S)-3-bromo-2-trimethylsilyloxysuccinate with allyltributyltin in the presence of Eu(fod)3 was found to give diethyl (2R, 3R)-3-allyl-2-trimethylsilyloxysuccinate with high diastereoselectivity [(2R, 3R): (2R, 3S)= 8.6:1].

  在 Eu(fod)3存在下，用烯丙基三丁基锡对(2S, 3S)-3-溴-2-三甲基硅氧基琥珀酸二乙酯进行烯丙基化反应，发现可得到(2R, 3R)-3-烯丙基-2-三甲基硅氧基琥珀酸二乙酯，且具有很高的非对映选择性[(2R, 3R): (2R, 3S)= 8.6:1]。
• Nagano Hajimo, Kuno Yukie, J. Chem. Soc. Chem. Commun, (1994) N 8, S 987-988
  作者：Nagano Hajimo, Kuno Yukie

  DOI：——

  日期：——
• Stereocontrol in radical-mediated allylation of acyclic α-bromo-β-siloxy esters by complexation with lanthanide shift reagents Ln(fod)₃
  作者：Hajime Nagano、Yukie Kuno、Yuriko Omori、Mayumi Iguchi

  DOI：10.1039/p19960000389

  日期：——

  Stereoselectivity in the radical-mediated allylation of alpha-bromo-beta-siloxy esters 2 yielding alpha-allyl-beta-siloxy esters 3 (syn) and 4 (anti) was remarkably affected when the reaction was conducted in the presence of Ln(fod)(3) [= tris-(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyloctane-3,5-dionato)lanthanide]. In the allylation of alpha-bromo-beta-siloxysuccinate esters 2c and 2d affording preferentially syn-diastereoisomers 3c and 3d through chelated transition states a stoichiometric amount of the Lewis acid [Eu(fod)(3) or La(fod)(3)] was required in order to maximize the stereoselectivities, whereas in the reaction of alpha-bromo-beta-siloxybutanoate esters 2g and 2h and alpha-bromo-beta-siloxy-beta-phenylpropanoate ester 2i the effect induced by the coordination of Eu(fod)(3) to the ester group was catalytic.