(2S,3R)-3-羟基-L-异 | 127126-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2S,3R)-3-羟基-L-异
• 英文名称: (2S,3R)-α-methylthreonine
• 英文别名: (2S,3R)-2-amino-3-hydroxy-2-methylbutanoic acid；α-MeThr；α-methylthreonine
• CAS: 127126-06-1
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: NWZTXAMTDLRLFP-WUJLRWPWSA-N

物化性质

• 沸点：
  317.3±32.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (2R,3S,7R,7aS)-7-methoxy-2,3,7,7a-tetramethyl-5-oxotetrahydro-2H-oxazolo[4,3-b]oxazole-3-carboxylate 在 盐酸 、 methyloxirane 作用下， 以 水 、 乙醇 为溶剂， 反应 0.67h， 以43%的产率得到(2S,3R)-3-羟基-L-异
  参考文献：
  名称：

  α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine

  摘要：

  The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-L-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of alpha-methylthreonine by an alpha-alkylation reaction and in the synthesis of chiral alpha,beta-dehydroamino acid derivatives, using the tandem retro-O-Michael/gamma-alkylation reactions as key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.031

文献信息

• Asymmetric Synthesis of All Stereoisomers of α-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step
  作者：Harald Gröger、Friedrich Dietz

  DOI：10.1055/s-0029-1217140

  日期：——

  An efficient synthetic route to all four stereoisomers of α-methylthreonine has been established. Each type of stereoisomer has been isolated in diastereomerically pure form and with an enantiomeric excess of at least 86% ee. The key step in this multi-step synthesis is an enantioselective organocatalytic Steglich rearrangement reaction of O-acetylated azlactones. The Steglich rearrangement was also

  已经建立了针对α-甲基苏氨酸的所有四个立体异构体的有效合成途径。每种类型的立体异构体均已以非对映体纯的形式分离，对映体过量至少为86％ee。该多步合成中的关键步骤是O-乙酰化a内酯的对映选择性有机催化Steglich重排反应。Steglich重排也扩展到其他基板。 酰化-氨基酸-不对称催化-重排-立体选择性合成
• Moon, Sung-Hwan; Ohfune, Yasufumi, Journal of the American Chemical Society, 1994, vol. 116, # 16, p. 7405 - 7406
  作者：Moon, Sung-Hwan、Ohfune, Yasufumi

  DOI：——

  日期：——
• Novel Enantioselective Synthesis of α-Methylthreonines and α,β-Dimethylcysteines
  作者：Hui Shao、Jaimie K. Rueter、Murray Goodman

  DOI：10.1021/jo971983u

  日期：1998.7.1
• α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: application in the synthesis of all stereoisomers of α-methylthreonine
  作者：Alberto Avenoza、Jesús H. Busto、Francisco Corzana、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/j.tetasy.2003.12.001

  日期：2004.2

  The asymmetric synthesis of all stereoisomers of alpha-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different beta-substituted alpha-methylserines. (C) 2003 Elsevier Ltd. All rights reserved.
• α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine
  作者：Carlos Aydillo、Alberto Avenoza、Jesús H. Busto、Gonzalo Jiménez-Osés、Jesús M. Peregrina、María M. Zurbano

  DOI：10.1016/j.tetasy.2008.11.031

  日期：2008.12

  The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-L-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of alpha-methylthreonine by an alpha-alkylation reaction and in the synthesis of chiral alpha,beta-dehydroamino acid derivatives, using the tandem retro-O-Michael/gamma-alkylation reactions as key steps. (C) 2008 Elsevier Ltd. All rights reserved.