5-Deoxy-3,4-O-isopropyliden-L-lyxitol | 159247-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Deoxy-3,4-O-isopropyliden-L-lyxitol
• 英文别名: (1S)-1-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 159247-46-8
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: QIGIJTXKTYJENP-LYFYHCNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Deoxy-3,4-O-isopropyliden-L-lyxitol 在 lead(IV) acetate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以90%的产率得到(4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde

  摘要：

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.

  DOI：

  10.1007/bf01277638
• 作为产物：
  描述：

  2,3-O-isopropylidene-L-arabinose diethyl mercaptal 在 镍 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到5-Deoxy-3,4-O-isopropyliden-L-lyxitol
  参考文献：
  名称：

  Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde

  摘要：

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.

  DOI：

  10.1007/bf01277638

文献信息

• Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer
  作者：Manikandan Kadirvel、William T. Stimpson、Souad Moumene-Afifi、Biljana Arsic、Nicola Glynn、Nigel Halliday、Paul Williams、Peter Gilbert、Andrew J. McBain、Sally Freeman、John M. Gardiner

  DOI：10.1016/j.bmcl.2010.02.064

  日期：2010.4

  The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from D-mannitol via (2R)2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescenceinducing properties in the Vibrio harveyi BB170 strain. (C) 2010 Elsevier Ltd. All rights reserved.
• Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde
  作者：W. H. Binder、R. H. Prenner、W. Schmid

  DOI：10.1007/bf01277638

  日期：1994.6

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.