(2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid ethyl ester | 187652-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid ethyl ester
• 英文别名: ethyl (2R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-carboxylate
• CAS: 187652-69-3
• 化学式: C₉H₁₆O₇
• 分子量: 236.222
• InChiKey: ZKKDCTCHPCGDJR-JAGXHNFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid ethyl ester 在 Dowex-50W(H⁺) 作用下， 以 重水 为溶剂， 生成 3-deoxy-D-arabino-2-heptulopyranosonic acid
  参考文献：
  名称：

  A new and concise synthesis of 3-deoxy-D-arabino-2-heptulopyranosonic acid (DAH) and derivatives through the radical chemistry of Barton esters

  摘要：

  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

  DOI：

  10.1016/s0040-4039(96)02331-3
• 作为产物：
  描述：

  (2R,3R,4R)-2,3:4,5-Di-O-isopropylidene-2,3,4,5-tetrahydroxy-pentanoic acid 在 乙醇 、 Dowex-50W(H⁺) 、 水 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 (2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  A new and concise synthesis of 3-deoxy-D-arabino-2-heptulopyranosonic acid (DAH) and derivatives through the radical chemistry of Barton esters

  摘要：

  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

  DOI：

  10.1016/s0040-4039(96)02331-3

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。
• 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