甲基2,3-二羟基-2-甲基丙酸酯 | 147501-85-7

• 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
• 中文名称: 甲基2,3-二羟基-2-甲基丙酸酯
• 中文别名: 1-(叔-丁基氨基)-3-[2-[2-(3-甲基异噻唑-5-基)乙烯基]苯氧基]丙烷-2-醇
• 英文名称: methyl 2,3-dihydroxy-2-methylpropenoate
• 英文别名: methyl-2(S),3-dihydroxy-2-methyl propanoate；(S)-methyl 2,3-dihydroxy-2-methylpropanoate；(S)-2,3-dihydroxy-2-methyl-propionic acid methyl ester；methyl (S)-2,3-dihydroxy-2-methylpropanoate；(2S)-2,3-Dihydroxy-2-methyl-propanoic acid methyl ester；methyl (2S)-2,3-dihydroxy-2-methylpropanoate
• CAS: 147501-85-7
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: LDZHNDDCTKHCFG-YFKPBYRVSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  甲基2,3-二羟基-2-甲基丙酸酯 在 氯化亚砜 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以90%的产率得到(4S)-4-甲基-2-氧代-[1,3,2]二恶噻戊环-4-羧酸甲酯
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-α-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(01)00159-8
• 作为产物：
  描述：

  甲基丙烯酸甲酯 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 以90%的产率得到甲基2,3-二羟基-2-甲基丙酸酯
  参考文献：
  名称：

  甲基丙烯酸、Tiglic 和当归酸的酯和酰胺的不对称二羟基化：Sharpless 助记符也不例外！

  摘要：

  关于当归酸异丁酯的 Sharpless 不对称二羟基化 (SAD) 面部选择性的文献发现是矛盾的，部分与 Sharpless 助记符相冲突。我们系统地筛选了当归、tiglic 和甲基丙烯酸的酯和酰胺的 SAD。在 15 个反应中的 14 个反应中出现了对映体控制，在 tiglic acid 的 Weinreb 酰胺的 ee 达到 99% 时达到顶峰。所有非外消旋产物的绝对构型都是通过（立体）化学相关性建立的。无一例外，它们都符合 Sharpless 助记符。

  DOI：

  10.1002/ejoc.201403622

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.
• 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.
• Asymmetric Dihydroxylation of Esters and Amides of Methacrylic, Tiglic, and Angelic Acid: No Exception to the Sharpless Mnemonic!
  作者：Fabian Weber、Reinhard Brückner

  DOI：10.1002/ejoc.201403622

  日期：2015.4

  are contradictory and partly in conflict with the Sharpless mnemonic. We systematically screened the SAD of esters and amides of angelic, tiglic, and methacrylic acid. Enantiocontrol arose in 14 of the 15 reactions, culminating at 99 % ee for the Weinreb amide of tiglic acid. The absolute configurations of all the nonracemic products were established by (stereo)chemical correlations. Without exception

  关于当归酸异丁酯的 Sharpless 不对称二羟基化 (SAD) 面部选择性的文献发现是矛盾的，部分与 Sharpless 助记符相冲突。我们系统地筛选了当归、tiglic 和甲基丙烯酸的酯和酰胺的 SAD。在 15 个反应中的 14 个反应中出现了对映体控制，在 tiglic acid 的 Weinreb 酰胺的 ee 达到 99% 时达到顶峰。所有非外消旋产物的绝对构型都是通过（立体）化学相关性建立的。无一例外，它们都符合 Sharpless 助记符。