L-ribono-lactone | 19774-08-4

• 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: L-ribono-lactone
• 英文别名: 2-C-Methyl-L-ribo-pentonsaeure-γ-lacton , 'α'-L-Glucosaccharinsaeure-lacton；2-C-methyl-L-ribono-1,4-lactone；(3S,4S,5S)-3,4-Dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one；(3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
• CAS: 19774-08-4
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: WJBVKNHJSHYNHO-FKZODXBYSA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  338.3±11.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

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：

  (2R,3S,4S,5R)-2-[(dibenzylamino)methyl]oxane-2,3,4,5-tetrol 在 吡啶 、 氢氧化钾 、 copper(II) sulfate 、 三氟乙酸 、 calcium oxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 硫酸 、 水 为溶剂， 反应 24.0h， 生成 L-ribono-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

• DIASTEREOSELECTION IN A DIRECTED CROSSED ALDOL REACTION BETWEEN TWO POLYOXYGENATED KETONES EMPLOYING TIN(II) ENOLATES. A FACILE STEREOSELECTIVE SYNTHESIS OF ETHYL 2-<i>C</i>-METHYL-DL-LYXOFURANOSIDE
  作者：Rodney W. Stevens、Teruaki Mukaiyama

  DOI：10.1246/cl.1983.595

  日期：1983.4.5

  Tin(II) enolates of 1,3-dihydroxy-2-propanone derivatives react with a second ketone, methyl pyruvate, under mild conditions to afford the corresponding anti-crossed aldol products in moderate to excellent yields. Facile elaboration to the branched-chain sugar, ethyl 2-C-methyl-DL-lyxofuranoside, was demonstrated.

  1,3-二羟基-2-丙酮衍生物的锡 (II) 烯醇化物与第二种酮丙酮酸甲酯在温和条件下反应，以中等至极好的产率提供相应的抗交叉羟醛产物。证明了对支链糖乙基 2-C-甲基-DL-lyxofuranoside 的简单加工。
• Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
  作者：Kathrine V. Booth、Filipa P. da Cruz、David J. Hotchkiss、Sarah F. Jenkinson、Nigel A. Jones、Alexander C. Weymouth-Wilson、Robert Clarkson、Thomas Heinz、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.10.013

  日期：2008.10

  Readily crystallized 2-C-methyl-D-ribono-1,4-lactone is formed in a one-pot procedure from D-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-L-ribono-1,4-lactone is similarly produced from L-glucose. 3,4-O-Isopropylidene-2-C-methyl-D-arabinono-1,5-lactone and 2-C-methyl-D-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-D-ribulose derived from D-erythronolactone; the enantiomeric arabinonolactones are similarly available from L-erythronolactone. (C) 2008 Elsevier Ltd. All rights reserved.