2-C-methyl-D-threono-1,4-lactone | 18548-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-C-methyl-D-threono-1,4-lactone
• 英文别名: (3S,4R)-3,4-dihydroxy-3-methyloxolan-2-one
• CAS: 18548-45-3
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: OHTGZAWPVDWARE-WUJLRWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  乙酸酐 、 2-C-methyl-D-threono-1,4-lactone 在 4-二甲氨基吡啶 吡啶 作用下， 反应 3.0h， 以74%的产率得到2,3-di-0-acetyl-2-C-methyl-D-threono-1,4-lactone
  参考文献：
  名称：

  WO2007/25304

  摘要：

  公开号：
• 作为产物：
  描述：

  1-deoxy-1-(N,N-dimethylamino)-D-xylulose 在 水 、 calcium oxide 作用下， 以 水 为溶剂， 反应 16.0h， 生成 2-C-methyl-D-threono-1,4-lactone
  参考文献：
  名称：

  WO2007/25304

  摘要：

  公开号：

文献信息

• An Efficient Method for the Preparation of Chiral Synthons Starting from Racemic Compounds by Way of Asymmetric Synthesis
  作者：Shu Kobayashi、Isamu Shiina、Jun Izumi、Teruaki Mukaiyama

  DOI：10.1246/cl.1992.373

  日期：1992.3

  Optically active α-alkoxy-α-methyl-β-hydroxy ester derivatives are prepared starting from racemic α-alkoxy propionic acid ester derivatives by way of asymmetric aldol reaction of the corresponding achiral intermediates. (−)-2-C-Methyl-D-threono-1,4-lactone is conveniently synthesized by using this methodology.

  旋光α-烷氧基-α-甲基-β-羟基酯衍生物由外消旋α-烷氧基丙酸酯衍生物通过相应非手性中间体的不对称羟醛反应制备。(-)-2-C-Methyl-D-threono-1,4-lactone 可以使用这种方法方便地合成。
• Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide
  作者：David J. Hotchkiss、Raquel Soengas、Kathrine V. Booth、Alexander C. Weymouth-Wilson、Vanessa Eastwick-Field、George W.J. Fleet

  DOI：10.1016/j.tetlet.2006.11.137

  日期：2007.1

  Saccharinic acids, branched 2-C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; D-galactose and D-glucose are converted to 2-C-methyl-D-lyxono-1,4-lactone (with a small amount of 2-C-methyl-D-xylono-1,4-lactone) and 2-C-methyl-D-ribono-1,4-lactone. Inversion of configuration at C-4 of the branched lactones allows access to 2-C-methyl-L-ribono-1,4-lactone and 2-C-methyl-L-lyxono-1,4-lactone, respectively. D-Xylose affords 2-C-methyl-D-threono-1,4-lactone and 2-C-methyl-D-erythrono-1,4-lactone, whereas L-arabinose, under similar conditions, gave the enantioiners 2-C-methyl-L-lactone-1,4-lactone and 2-C-methyl-L-erythrono-1,4-lactone. (c) 2006 Published by Elsevier Ltd.
• Enantioselective Synthesis of the a-Hydroxy-a-methyl-b-hydroxy Units via Asymmetric Aldol Reaction
  作者：Teruaki Mukaiyama、Isamu Shiina、Jun Izumu、Shu Kobayashi

  DOI：10.3987/com-93-s(t)138

  日期：——

  The alpha-hydroxy-alpha-methyl-beta-hydroxy units are enantioselectively prepared by way of asymmetric aldol reactions between both achiral beta,beta-disubstituted silyl enolates and aldehydes. (-)-2-C-Methyl-D-threono-1,4-lactone is conveniently synthesized by using this reaction.
• An Efficient Preparation of 2-<i>C</i>-Methyl-<scp>d</scp>-Erythritol 4-Phosphoric Acid and Its Derivatives
  作者：Klaus Kis、Juraithip Wungsintaweekul、Wolfgang Eisenreich、Meinhart H. Zenk、Adelbert Bacher

  DOI：10.1021/jo9905118

  日期：2000.1.1