Sodium (2R*,3R*)-3-hydroxy<2-(2)H>butanoate | 79069-09-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Sodium (2R*,3R*)-3-hydroxy<2-(2)H>butanoate
• CAS: 79069-09-3
• 化学式: C₄H₇O₃*Na
• 分子量: 127.08
• InChiKey: NBPUSGBJDWCHKC-HGQXRRHPSA-M

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 Sodium (2R*,3R*)-3-hydroxy<2-(2)H>butanoate 在 N,N-二甲基丙烯基脲 作用下， 反应 1.3h， 生成 Ethyl (2R*,3R*)-3-hydroxy<2-(2)H>butanoate
  参考文献：
  名称：

  Diastereoselectivity in the Protonation of Ester Enolates. The Importance of Aggregation with LDA

  摘要：

  The effect of aggregation on the stereochemistry of electrophilic attack on ester enolate anions has been studied by comparing the diastereoselectivity of protonation of the LDA-generated dianion bf I 1 in THF/DMPU with the H/D exchange of 3 under non-ion-pairing conditions. The LDA results are consistent with proton transfer to the:enolate occurring preferentially from the tightly complexed secondary amine. Proton sources of varying steric requirements produced the same diastereomeric ratio, 63:37 2R*,3R*/2R*,3S* of 2. Added BuLi and the omission of DMPU gave the same diastereomeric mixture. In contrast to the LDA results, ethyl beta-hydroxy- and beta-alkoxybutyrates undergo base-catalyzed H/D exchange largely through antiperiplanar transition states, with diastereoselectivity opposite of that found in-the LDA-enolate protonation. Thus, the geometry of the LDA-enolate aggregate, rather than steric and electronic factors in the monomer, is responsible for the stereochemistry of enolate anion protonation. The lower diastereoselectivity in the H/D exchange of 6 in THF is accounted forby ion-pairing effects, as the use of Me(4)NOD produced 92% of the 2R*,3R* diastereomer; Use of polar solvents in the H/D exchange also raised the diastereoselectivity to a 10:1 ratio or higher.

  DOI：

  10.1021/jo00116a046

文献信息

• Stereospecific reduction of 2,3-epoxybutanoic acid. Synthesis of (R,R)- and (S,S)-3-hydroxybutanoic-2-d acid and S-tert-butyl 3-acetoxythiobutanoate-2-d
  作者：Jerry R. Mohrig、Pieter J. Vreede、Steve C. Schultz、Carol A. Fierke

  DOI：10.1021/jo00336a003

  日期：1981.11