3-deoxy-D-arabino-2-heptulopyranosonic acid | 29873-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-D-arabino-2-heptulopyranosonic acid
• 英文别名: ammonium 3-deoxy-D-arabino-heptulosonate；3-Desoxy-D-arabino-heptulosansaeure；(4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-carboxylic acid
• CAS: 29873-77-6
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: ZHHLKJCKIUIROE-KENYUPALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-deoxy-D-arabino-2-heptulopyranosonic acid 在 盐酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 乙酰氯 作用下， 以 吡啶 、 甲醇 、 乙醚 、 苯 为溶剂， 反应 36.33h， 生成 Methyl β-(2,6-Anhydro-4,5,7-tri-O-acetyl-3-deoxy-D-arabino-heptulopyranosid)onate
  参考文献：
  名称：

  Chemical inhibition of dehydroquinate synthase

  摘要：

  DOI：

  10.1021/ja00187a048
• 作为产物：
  描述：

  2,3-二氟-6-硝基苯胺 在 吡啶 、 dirhodium tetraacetate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 3-deoxy-D-arabino-2-heptulopyranosonic acid
  参考文献：
  名称：

  β-氧-α-重氮羰基化合物。三，Rh 2（AcO）4介导的β-乙酰氧基-α-重氮酯的分解。在合成天然3-脱氧-2-酮醛糖酸（KDO和DAH）中的应用

  摘要：

  β-乙酰氧基-α-重氮酯通过与四乙酸二钠反应定量地生成α-烯醇乙酸酯。该反应用于通过烯醇的转化制备主要的天然化合物3-脱氧-D-阿拉伯糖-2-庚酸（DAH，1）和3-脱氧-D-甘露糖-2-辛酸（KDO，2）乙酸官能化为相应的酮。

  DOI：

  10.1016/s0040-4039(00)73473-3

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。
• An In-Depth Study on Ring-Closing Metathesis of Carbohydrate-Derived α-Alkoxyacrylates:  Efficient Syntheses of DAH, KDO, and 2-Deoxy-β-KDO
  作者：Koen F. W. Hekking、Marcel A. H. Moelands、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo060913x

  日期：2006.8.1

  Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-β-KDO are described. Ring-closing metathesis (RCM) of highly functionalized α-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting

  描述了通往DAH，KDO和2-deoxy-β-KDO的新颖，有效的合成途径。高度官能化的α-烷氧基丙烯酸酯片段的闭环复分解（RCM）导致了一系列合成上通用的氧杂环中间体。从可商购的被保护的糖开始，所得烯醇醚双键的进一步官能化和随后的脱保护以高的总收率提供了天然产物。
• G.L.C.-M.S. of partially methylated and acetylated derivatives of 3-deoxy-2-ketoaldonic acids and 3-deoxy-alditols
  作者：Angelika Tacken、Helmut Brade、Paul Kosma、Daniel Charon

  DOI：10.1016/0008-6215(87)80262-8

  日期：1987.9

  Abstract Partially methylated and acetylated 3-deoxyoctitols and 3-deoxyheptitols were prepared from synthetic derivatives of 3-deoxy- d -manno-octulosonic acid and 3-deoxy- d -arabino-heptulosonic acid, espectively, by derivatisation procedures used in methylation analysis (hydrolysis, carbonyl- and carboxyl-reduction, methylation, and acetylation). The compounds so obtained were characterised by

  摘要分别通过甲基化分析中使用的衍生化程序，分别由3-脱氧-d-甘露糖辛酸和3-脱氧-d-阿拉伯糖庚酸合成衍生物制备了部分甲基化和乙酰化的3-脱氧辛醇和3-脱氧庚糖醇（水解，羰基和羧基还原，甲基化和乙酰化）。如此获得的化合物用glc和glc-ms表征，并报道了它们的保留时间和片段化模式。
• Dondoni, Alessandro; Marra, Alberto; Merino, Pedro, Journal of the American Chemical Society, 1994, vol. 116, # 8, p. 3324 - 3336
  作者：Dondoni, Alessandro、Marra, Alberto、Merino, Pedro

  DOI：——

  日期：——
• The use of Aspergillus terreus extracts in the preparative synthesis of 2-keto-3-deoxy-ulosonic acids
  作者：Claudine Augé、Véronique Delest

  DOI：10.1016/0957-4166(95)00090-c

  日期：1995.4

  Pure 2-keto-3-deoxy-ulosonic acids, KDGal (1), DAH (2) and its 5-epimer (3) were prepared on preparative scales through diastereoselective aldol reactions of pyruvate respectively with D-glyceraldehyde, D-erythrose and D-threose, catalyzed by Aspergillus terreus extracts; from 2-deoxy-D-ribose, 5-deoxy-KDO (4) could be obtained in a lower yield, with a diastereomeric excess of 72%.