ethyl (2S,3R)-2,3-dihydroxy-4,4-dimethyl-propanoate | 206257-62-7

• 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: ethyl (2S,3R)-2,3-dihydroxy-4,4-dimethyl-propanoate
• 英文别名: ethyl (2S,3R)-2,3-dihydroxy-4,4-dimethylpentanoate
• CAS: 206257-62-7
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: WKFJIVZMZFJBIT-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3R)-2,3-dihydroxy-4,4-dimethyl-propanoate 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 硫酸 、 lithium bromide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (2R,3R)-2-Bromo-3-hydroxy-4,4-dimethyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  通过环状硫酸盐中间体高效合成手性α，β-环氧酯

  摘要：

  手性α，β环氧酯的有效的合成1从手性2,3- dihydroxyester 2已经研制成功。将酯2转化为相应的环状硫酸盐3，将其在室温下用THF中的LiBr或在丙酮中的Bu 4 NBr打开，以提供2-溴-3-羟基酯4。在甲醇中在低温下用K 2 CO 3处理4，得到的α，β-环氧酯1的总收率极好，且ee与起始二醇相同。

  DOI：

  10.1016/s0040-4039(98)00190-7
• 作为产物：
  描述：

  3-tert-butyl-acrylic acid ethyl ester 在 甲基磺酰胺 、 potassium carbonate potassium osmate(VI) 、 K₂[Fe(CN)6] 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 水 、 叔丁醇 为溶剂， 以68%的产率得到ethyl (2S,3R)-2,3-dihydroxy-4,4-dimethyl-propanoate
  参考文献：
  名称：

  Improved preparation of β-hydroxy-α-amino acids: direct formation of sulfates by sulfuryl chloride

  摘要：

  Two beta-(alkyl)-beta-hydroxy-alpha-amino acids [alkyl = But, BnO-(CH2)(3)-] have been synthesized by a sequence based on Sharpless asymmetric dihydroxylation. The key sulfate intermediates were prepared from enantiomerically enriched diols by direct treatment with sulfuryl chloride. The scope and the appropriate conditions for sulfate formation have also been studied. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.10.013

文献信息

• 1,2-Asymmetric induction in radical reactions. Deuteration and allylation reactions of β-oxy-α-bromo esters
  作者：Dennis P. Curran、P.S. Ramamoorthy

  DOI：10.1016/s0040-4020(01)80402-6

  日期：1993.5

  Chiral radicals were generated by halogen abstraction reactions of β-oxy-α-bromo esters and their asymmetric deuteration and allylation reactions were studied.

  通过β-氧基-α-溴代酸酯的卤素抽象反应生成手性自由基，并研究了它们的不对称氘代和烯丙基化反应。
• Efficient synthesis of chiral α,β-epoxyesters via a cyclic sulfate intermediate
  作者：Linli He、Hoe-Sup Byun、Robert Bittman

  DOI：10.1016/s0040-4039(98)00190-7

  日期：1998.4

  An efficient synthesis of chiral α,β-epoxyester 1 from chiral 2,3-dihydroxyester 2 has been developed. Ester 2 is converted to the corresponding cyclic sulfate 3, which is opened with either LiBr in THF or Bu4NBr in acetone at rt to furnish 2-bromo-3-hydroxyester 4. Treatment of 4 with K2CO3 in methanol at low temperature gives α,β-epoxyester 1 in excellent overall yield and in the same ee as in the

  手性α，β环氧酯的有效的合成1从手性2,3- dihydroxyester 2已经研制成功。将酯2转化为相应的环状硫酸盐3，将其在室温下用THF中的LiBr或在丙酮中的Bu 4 NBr打开，以提供2-溴-3-羟基酯4。在甲醇中在低温下用K 2 CO 3处理4，得到的α，β-环氧酯1的总收率极好，且ee与起始二醇相同。
• Improved preparation of β-hydroxy-α-amino acids: direct formation of sulfates by sulfuryl chloride
  作者：Mònica Alonso、Antoni Riera

  DOI：10.1016/j.tetasy.2005.10.013

  日期：2005.11

  Two beta-(alkyl)-beta-hydroxy-alpha-amino acids [alkyl = But, BnO-(CH2)(3)-] have been synthesized by a sequence based on Sharpless asymmetric dihydroxylation. The key sulfate intermediates were prepared from enantiomerically enriched diols by direct treatment with sulfuryl chloride. The scope and the appropriate conditions for sulfate formation have also been studied. (c) 2005 Published by Elsevier Ltd.