2,3-O-isopropylidene-3-C-methyl-L-erythrono-1,4-lactone | 114877-78-0

• 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-3-C-methyl-L-erythrono-1,4-lactone
• 英文别名: (3aS,6aS)-2,2,3a-trimethyl-4,6a-dihydrofuro[3,4-d][1,3]dioxol-6-one
• CAS: 114877-78-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: PWIMWAFHIYTCCN-XRGYYRRGSA-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-3-C-methyl-L-erythrono-1,4-lactone 在 二甲基氯化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (4R,5R)-5-Methoxymethoxymethyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid
  参考文献：
  名称：

  氯甲基铝2（2-丙烯基）苯胺-将内酯转化为受保护的羟基酸的便捷试剂

  摘要：

  标题试剂与γ和δ内酯反应生成羟基酰胺，可轻松转化为受保护的N-酰基吲哚。轻度皂化可提供吲哚和受保护的羟基酸。

  DOI：

  10.1016/s0040-4039(00)95503-5
• 作为产物：
  描述：

  2,3-O-isopropylidene-3-C-methyl-L-erythrpfuranose 在 重铬酸吡啶 、 三氟乙酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到2,3-O-isopropylidene-3-C-methyl-L-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

• Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
  作者：K. Victoria Booth、Sarah F. Jenkinson、Daniel Best、Fernando Fernández Nieto、Ramón J. Estévez、Mark R. Wormald、Alexander C. Weymouth-Wilson、George W.J. Fleet

  DOI：10.1016/j.tetlet.2009.06.098

  日期：2009.9

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.
• Application of (chloromethyl)aluminum 2-(2-propenyl)anilide in the conversion of .gamma.- and .delta.-lactones into protected hydroxy acids
  作者：Anthony G. M. Barrett、Barend C. B. Bezuidenhoudt、Dashyant Dhanak、Alan F. Gasiecki、Amy R. Howell、Albert C. Lee、Mark A. Russell

  DOI：10.1021/jo00275a015

  日期：1989.7
• Chloromethylaluminum 2 (2-propenyl)anilide - a convenient reagent for the conversion of lactones into protected hydroxy acids
  作者：Anthony G.M. Barrett、Dashyant Dhanak

  DOI：10.1016/s0040-4039(00)95503-5

  日期：1987.1

  The title reagent reacts with γ and δ lactones to provide hydroxy amides which can be easily converted into protected N-acyl indoles. Mild saponification provides indole and the protected hydroxy acid.

  标题试剂与γ和δ内酯反应生成羟基酰胺，可轻松转化为受保护的N-酰基吲哚。轻度皂化可提供吲哚和受保护的羟基酸。
• 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.