2,3-O-isopropylidene-2-C-methyl-erythrono-1,4-lactone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-2-C-methyl-erythrono-1,4-lactone
• 英文别名: (3aS,6aS)-2,2,3a-trimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: IUOBLUOQEZUCIP-XNCJUZBTSA-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：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-2-C-methyl-erythrono-1,4-lactone 在 甲醇 作用下， 以76%的产率得到(2S,3S)-2,3-dihydroxy-2-methyl-γ-butyrolactone
  参考文献：
  名称：

  A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the Leaf-Closing Substance Potassium (±)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate

  摘要：

  A series of 1,2-dioxanes 3 were ring-opened with Co-(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2C-D-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.

  DOI：

  10.1021/jo900392y
• 作为产物：
  描述：

  2,3-O-isopropylidene-2-C-methyl-erythrofuranose 在 重铬酸吡啶 、 三氟乙酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到2,3-O-isopropylidene-2-C-methyl-erythrono-1,4-lactone
  参考文献：
  名称：

  A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the Leaf-Closing Substance Potassium (±)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate

  摘要：

  A series of 1,2-dioxanes 3 were ring-opened with Co-(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2C-D-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.

  DOI：

  10.1021/jo900392y

文献信息

• WO2007/25304
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] PROCESS FOR PREPARING SACCHARINIC ACIDS AND LACTONES<br/>[FR] PROCEDE DE PREPARATION D'ACIDES SACCHARINIQUES ET DE LACTONES
  申请人：CHANCELLORS MASTERS AND SCHOLA

  公开号：WO2007025304A2

  公开（公告）日：2007-03-01

  [EN] An improved process for preparing a saccharinic acid or lactone is disclosed that utilizes the well-known Amadori rearrangement reaction. The synthesis utilizes protected or unprotected sugars or their analogues as starting materials, and reagents not previously utilized to afford increased product yields in decreased reaction time.
  [FR] L'invention concerne un procédé amélioré de préparation d'acide saccharinique ou de lactone, qui utilise la réaction bien connue de réarrangement d'Amadori. Le procédé de synthèse utilise comme matières premières des sucres protégés ou non protégés ou leurs analogues, ainsi que les réactifs n'ayant pas été utilisés précédemment pour obtenir des rendements de produit accrus en un temps de réaction réduit.
• A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the Leaf-Closing Substance Potassium (±)-(2<i>R</i>,3<i>R</i>)-2,3,4-Trihydroxy-2-methylbutanoate
  作者：Daniel Sejer Pedersen、Tony V. Robinson、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo900392y

  日期：2009.6.5

  A series of 1,2-dioxanes 3 were ring-opened with Co-(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2C-D-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.