(3R,4S)-3,4-dihydroxy-3-methyldihydrofuran-2(3H)-one | 160224-89-5

• 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: (3R,4S)-3,4-dihydroxy-3-methyldihydrofuran-2(3H)-one
• 英文别名: (+)-2-C-methyl-L-threono-1,4-lactone；2-C-methyl-L-threono-1,4-lactone；2-C-methyl-D-threono-1,4-lactone；(3R,4S)-3,4-dihydroxy-3-methyloxolan-2-one
• CAS: 160224-89-5
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: OHTGZAWPVDWARE-WVZVXSGGSA-N

物化性质

• 沸点：
  254.0±7.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

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 、 (3R,4S)-3,4-dihydroxy-3-methyldihydrofuran-2(3H)-one 在 4-二甲氨基吡啶 吡啶 作用下， 反应 3.0h， 以63%的产率得到2,3-di-O-acetyl-2-C-methyl-L-threono-1,4-lactone
  参考文献：
  名称：

  WO2007/25304

  摘要：

  公开号：
• 作为产物：
  描述：

  S-ethyl (2R,3R)-2-benzyloxy-3-hydroxy-3-methoxycarbonylbutanethioate 在 palladium on activated charcoal 、 镍 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 (3R,4S)-3,4-dihydroxy-3-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Enantioselective synthesis of both diastereomers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated

  摘要：

  Diastereo- and enantioselective synthesis of both diastereomers, including the alpha-alkoxy-beta-hydroxy-beta-methyl(phenyl) units, was performed by using chiral tin(II) Lewis acid-mediated asymmetric aldol reactions of a-alkoxy silyl enol ethers with alpha-ketoesters. (S)-1-Propyl-2-[(1,2,3,4-tetrahydroisoquinolinyl))methyl]pyrrolidine (13), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene (9) with aldehydes for the synthesis of optically active syn-a,p-dihydroxy thioester derivatives. (-)-2-C-Methyl-D-erythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.

  DOI：

  10.1016/s0040-4020(01)85531-9

文献信息

• 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 both diastereomers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated
  作者：Shū Kobayashi、Mineko Horibe、Yumi Saito

  DOI：10.1016/s0040-4020(01)85531-9

  日期：——

  Diastereo- and enantioselective synthesis of both diastereomers, including the alpha-alkoxy-beta-hydroxy-beta-methyl(phenyl) units, was performed by using chiral tin(II) Lewis acid-mediated asymmetric aldol reactions of a-alkoxy silyl enol ethers with alpha-ketoesters. (S)-1-Propyl-2-[(1,2,3,4-tetrahydroisoquinolinyl))methyl]pyrrolidine (13), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene (9) with aldehydes for the synthesis of optically active syn-a,p-dihydroxy thioester derivatives. (-)-2-C-Methyl-D-erythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.
• WO2007/25304
  申请人：——

  公开号：——

  公开（公告）日：——