2-C-methyl-L-lyxono-1,4-lactone

• 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-L-lyxono-1,4-lactone
• 英文别名: (3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: WJBVKNHJSHYNHO-MRKVFDINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-O-异丙亚基-2-C-甲基-D-核糖酸-gamma-内酯 在 4-二甲氨基吡啶 、 氢氧化钾 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 吡啶 、 水 为溶剂， 生成 2-C-methyl-L-lyxono-1,4-lactone
  参考文献：
  名称：

  Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.11.137

文献信息

• [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.
• 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.