(S)-2,3-dihydroxy-2-methyl-propionic acid | 316373-88-3

• 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: (S)-2,3-dihydroxy-2-methyl-propionic acid
• 英文别名: (2s)-2,3-Dihydroxy-2-Methylpropanoic Acid
• CAS: 316373-88-3
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: DGADNPLBVRLJGD-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (S)-2,3-dihydroxy-2-methyl-propionic acid 生成 甲基2,3-二羟基-2-甲基丙酸酯
  参考文献：
  名称：

  Asymmetric synthesis of 2-alkyl-2,3-dihydroxypropionates from glycerol

  摘要：

  The preparation of optically active 2-substituted 2,3-dihydroxypropionates from glycerol is described.

  DOI：

  10.1016/s0957-4166(00)80504-2
• 作为产物：
  描述：

  (2S)-2,3-二羟基-N-甲氧基-N,2-二甲基丙酰胺 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (S)-2,3-dihydroxy-2-methyl-propionic acid
  参考文献：
  名称：

  An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

  摘要：

  This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00230-0

文献信息

• An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives
  作者：Alberto Avenoza、Carlos Cativiela、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/s0957-4166(01)00230-0

  日期：2001.6

  This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Preparation of 2(R) and 2(S) methyl-2-methylglycerates
  作者：Juan B. Rodríguez、Sanford P. Markey、Herman Ziffer

  DOI：10.1016/s0957-4166(00)86020-6

  日期：1993.1

  Optically pure samples of both enantiomers of methyl 2,3-dihydroxy-2-methylpropanoate were prepared by a chromatographic separation of their (-)-menthyl esters followed by hydrolysis and methylation. Their absolute stereochemistries were established by conversion into their 3-0-acetyl derivatives, compounds of established configuration. NMR and CG-MS methods of determining the optical purities of the diols are described.
• Enantioselective Synthesis of α-Methyl-<scp>d</scp>-cysteine and Lanthionine Building Blocks via α-Methyl-<scp>d</scp>-serine-β-lactone
  作者：Nicole D. Smith、Murray Goodman

  DOI：10.1021/ol034025p

  日期：2003.4.1

  [GRAPHICS]We report here the enantioselective synthesis of Boc-alpha-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regloselective ring opening of key intermediate Boc-alpha-methyl-D-serine-beta-lactone.
• Asymmetric synthesis of 2-alkyl-2,3-dihydroxypropionates from glycerol
  作者：Kuang-Fu Yen、Biing-Jiun Uang

  DOI：10.1016/s0957-4166(00)80504-2

  日期：1992.6

  The preparation of optically active 2-substituted 2,3-dihydroxypropionates from glycerol is described.
• Enantioselective synthesis of (S)- and (R)-α-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals
  作者：Alberto Avenoza、Carlos Cativiela、Francisco Corzana、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/s0957-4166(01)00159-8

  日期：2001.4

  This report describes the synthesis of enantiomerically pure (S)- and (R)-alpha -methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary alpha -amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-alpha -methylserinal building blocks. (C) 2001 Elsevier Science Ltd. All rights reserved.