Methyl (2R,3R,4R)-2,3:4,5-di-O-isopropylidene-2,3,4,5-tetrahydroxy-pentanoate | 145649-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (2R,3R,4R)-2,3:4,5-di-O-isopropylidene-2,3,4,5-tetrahydroxy-pentanoate
• 英文别名: methyl (4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 145649-97-4
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: LUCOZUIPTNMMHE-IWSPIJDZSA-N

物化性质

• 沸点：
  291.3±40.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl (2R,3R,4R)-2,3:4,5-di-O-isopropylidene-2,3,4,5-tetrahydroxy-pentanoate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.5h， 以90%的产率得到(2R,3R,4R)-2,3:4,5-Di-O-isopropylidene-2,3,4,5-tetrahydroxy-pentanoic acid
  参考文献：
  名称：

  自由基反应的发明。第三十八部分 汽车☐水杨酸与丙烯酰胺的同系物以及3-脱氧-D-阿拉伯糖-2-庚基磺酸（DAH）及其4-表位分子的合成研究

  摘要：

  由N-羟基-2-硫代吡啶酮的O-酰基衍生物产生的烷基在室温下加到丙烯酰胺上，形成结晶的2-（2-吡啶基硫烷基）-car☐酰胺。在室温下通过硼化镍将后者脱硫，以定量收率得到伯酰胺。通过类似的自由基化学方法，从商业D-核糖内酯有效合成了3-Deoxy-D-阿拉伯糖-2-庚基磺酸（DAH），其4-表位及其衍生物。

  DOI：

  10.1016/s0040-4020(97)00543-7
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 D-(+)-核糖酸-1,4-内酯 在 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 48.0h， 以82%的产率得到Methyl (2R,3R,4R)-2,3:4,5-di-O-isopropylidene-2,3,4,5-tetrahydroxy-pentanoate
  参考文献：
  名称：

  From carbohydrates to carbocycles: radical routes via Tellurium derivatives

  摘要：

  D-Ribose was transformed to its protected tosylate 15, followed by a Wittig-reaction to give 16 as a 3:1 mixture of the corresponding Z and E isomers. This mixture was then transformed to the anisyltelluride 17 and the latter cyclized in a radical exchange reaction to a mixture of the carbocycles 18a and 18b (in a 17:2 ratio). The major product 18a was then transformed to various chiral cyclopentane derivatives including the cyclopentenone-derivative 23. Various other carbohydrate-based approaches have also been explored.

  DOI：

  10.1016/s0040-4020(01)85616-7

文献信息

• The invention of radical reactions. Part XXXVIII. Homologation of car☐ylic acids with acrylamide and synthetic studies of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and its 4-epimer
  作者：Derek H.R. Barton、Wansheng Liu

  DOI：10.1016/s0040-4020(97)00543-7

  日期：1997.8

  Alkyl radicals generated from O-acyl derivatives of N-hydroxy-2-thiopyridone added onto acrylamide at room temperature to form crystalline 2-(2-pyridylsulfanyl)-car☐amides. Desulfurization of the latter by nickel boride at room temperature afforded primary amides in quantitative yield. 3-Deoxy-D-arabino-2-heptulosonic acid (DAH), its 4-epimer, and their derivatives were effectively synthesized from

  由N-羟基-2-硫代吡啶酮的O-酰基衍生物产生的烷基在室温下加到丙烯酰胺上，形成结晶的2-（2-吡啶基硫烷基）-car☐酰胺。在室温下通过硼化镍将后者脱硫，以定量收率得到伯酰胺。通过类似的自由基化学方法，从商业D-核糖内酯有效合成了3-Deoxy-D-阿拉伯糖-2-庚基磺酸（DAH），其4-表位及其衍生物。
• From carbohydrates to carbocycles: radical routes via Tellurium derivatives
  作者：Derek H.R. Barton、José Camara、Xiaoqin Cheng、Stephane D. Géro、Joseph Cs. Jaszberenyi、Beatrice Quiclet-Sire

  DOI：10.1016/s0040-4020(01)85616-7

  日期：1992.1

  D-Ribose was transformed to its protected tosylate 15, followed by a Wittig-reaction to give 16 as a 3:1 mixture of the corresponding Z and E isomers. This mixture was then transformed to the anisyltelluride 17 and the latter cyclized in a radical exchange reaction to a mixture of the carbocycles 18a and 18b (in a 17:2 ratio). The major product 18a was then transformed to various chiral cyclopentane derivatives including the cyclopentenone-derivative 23. Various other carbohydrate-based approaches have also been explored.
• A new and concise synthesis of 3-deoxy-D-arabino-2-heptulopyranosonic acid (DAH) and derivatives through the radical chemistry of Barton esters
  作者：Derek H.R. Barton、Wansheng Liu

  DOI：10.1016/s0040-4039(96)02331-3

  日期：1997.1

  Barton ester-based radical chemistry was applied in the synthesis of 3-deoxy-D-orobino-2-heptulopyranosonic acid (DAH) from commercial D-ribonolactone, The radical reaction with olefin 2, followed by aqueous work-up, provided the seven-carbon sugar compounds 5 and 6 (3:1) in 60% yield. Removal of the isopropylidene groups from 5 and hydrolysis of the ethyl ester yielded the DAH barium salt quantitatively. Copyright (C) 1996 Elsevier Science Ltd