D-threo-[2,5]hexodiulosonic acid; calcium salt (2:1) | 24940-63-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: D-threo-[2,5]hexodiulosonic acid; calcium salt (2:1)
• 英文别名: (3S,4S)-3,4,6-trihydroxy-2,5-dioxo-hexanoic acid; calcium salt (2:1)；D-threo-[2,5]hexodiulosonic acid ; calcium salt；D-threo-[2,5]Hexodiulosonsaeure; Calcium-Salz；calcium bis(hydrogen D-threo-hexo-2,5-diulosonate)
• CAS: 24940-63-4
• 化学式: 2C₆H₇O₇*Ca
• 分子量: 422.313
• InChiKey: RAONXBSQKIUVSJ-HJXLNUONSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.79
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134.96
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  D-threo-[2,5]hexodiulosonic acid; calcium salt (2:1) 在 calcium hydroxide 作用下， 生成 L(+)-赤藓酮糖(水合)
  参考文献：
  名称：

  糖基糖与α-金属化异氰基乙酸酯反应合成支链糖1

  摘要：

  摘要在强碱性介质中将异氰基乙酸乙酯添加到糖基蔗糖1,2：5,6-二-O-异亚丙基-α-d-核糖-六呋喃糖-3-ulose（1）和1,2-O-异亚丙基-5 -O-三苯甲基-d-赤-戊基-3-戊糖（2）给出不饱和衍生物（E）-和（Z）-3-脱氧-3-C-乙氧基羰基（甲酰氨基）亚甲基-1,2：5， 6-二-O-异亚丙基-α-d-葡糖呋喃糖（3和4）和（E）-3-脱氧-3-C-乙氧基羰基（甲酰氨基）亚甲基-1,2-O-异亚丙基-5-O-三苯甲基-α-d-呋喃核糖（5）。在弱碱性介质中，异氰基乙酸乙酯和1以良好的收率得到3-C-乙氧基羰基（甲酰胺基氨基）甲基-1，2：5，6-二-O-异亚丙基-α-d-铝呋喃糖（12）。用四氧化将3和4氧化为3- C-乙氧基-1,2,5,6-二-O-异亚丙基-α-d-葡糖呋喃糖（17），随后还原为3-C-（R ）-1′，2'-二羟乙基-1,2：5,6-二-O-异亚丙基

  DOI：

  10.1016/s0008-6215(00)80365-1

文献信息

• 2,5-Dicarbonyl sugars: New intermediates for synthesising heterocyclic rings. I. Synthesis of 4(1H)-pyridazinone derivatives from dicarbonyl sugars.
  作者：KATSUMI IMADA、KAZUO ASANO

  DOI：10.1248/cpb.22.1691

  日期：——

  2, 5-Dicarbonyl sugars (5-keto-D-fructose and 2, 5-diketo-D-gluconate) prepared by bacterial oxidation, react with hydrazine hydrate to give 4 (1H)-pyridazinone derivatives. Treatment of 5-keto-D-fructose (D-threo-2, 5-hexodiulose) (I) with hydrazine hydrate yields 3, 6-dihydroxymethyl-4 (1H)-pyridazinone (III), which is identical with the reaction product of kojic acid with hydrazine. Treatment of 2, 5-diketo-D-gluconate (D-threo-2, 5-hexodiulosonate (II) with hydrazine hydrate yields a mixture of 3-hydroxymethyl-4 (1H)-pyridazinone-6-carboxylic acid (IV) and 6-hydroxymethyl-4 (1H)-pyridazinone-3-carboxylic acid (V), whose structures can be established by chemical and spectroscopic methods. The mechanisms of their formation are also discussed.

  通过细菌氧化法得到的2,5-二羰基糖（5-酮-D-果糖和2,5-二酮-D-葡糖酸）与水合肼反应生成4(1H)-吡嗪酮衍生物。5-酮-D-果糖（D-苏式-2,5-己二糖）（I）与水合肼反应生成3,6-二羟甲基-4(1H)-吡嗪酮（III），该产物与曲酸与肼的反应产物相同。2,5-二酮-D-葡糖酸（D-苏式-2,5-己二糖酸（II）与水合肼反应生成3-羟甲基-4(1H)-吡嗪酮-6-羧酸（IV）和6-羟甲基-4(1H)-吡嗪酮-3-羧酸（V）的混合物，其结构可通过化学和光谱方法确定。它们的形成机制也进行了讨论。
• 2,5-Dicarbonyl sugars: New intermediates for synthesising heterocyclic rings. II. Synthesis of N-substituted 5-Oxidopyridazinium derivatives from 2,5-diketo-D-gluconate.
  作者：KATSUMI IMADA

  DOI：10.1248/cpb.22.1732

  日期：——

  2, 5-Diketo-D-gluconate (I) (D-threo-2, 5-hexodiulosonate) reacted with mono substituted hydrazines yielding anhydro 1-substituted 3-hydroxymethyl-5-hydroxypyridazinium hydroxides (IIa-g) which were a type of zwitterionic heterocyclic compounds, relatively unknown. Their structures were confirmed by their microanalytical results and spectroscopic evidences. The intermediate in the formation of anhydro 3-hydroxymethyl-5-hydroxy-1-phenyl-pyridazinium hydroxide was obtained. The structure (VIIc) (tautomeric 5-phenylhydrazone of 4-deoxy-2, 5-hexodiulosonate-3-ene) could be substantiated by spectral data. The formation of IIa-g might be accounted for in terms of mono phenylhydrazone formation, enediol formation, β-hydroxycarbonyl elimination, decarboxylation and cyclization.

  2, 5-二酮-D-葡萄糖酸（I）（D-苏式-2, 5-己二酮酸）与单取代肼反应，生成无水1-取代3-羟甲基-5-羟基哒嗪氢氧化物（IIa-g），这是一种两性离子杂环化合物，相对而言，人们对其知之甚少。它们的结构通过微量分析结果和光谱证据得到证实。形成无水3-羟甲基-5-羟基-1-苯基-哒嗪氢氧化物的中间体已经获得。结构（VIIc）（4-脱氧-2, 5-己二酮酸-3-烯的5-苯基肼酮的同分异构体）可以通过光谱数据得到证实。IIa-g的形成可以用单苯肼酮的形成、烯二醇的形成、β-羟基羰基消除、脱羧和环化来解释。