D-erythrofuranose | 210230-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-erythrofuranose
• 英文别名: D-erythrose；erythrose；(3R,4R)-oxolane-2,3,4-triol
• CAS: 210230-59-4
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: FMAORJIQYMIRHF-HERZVMAMSA-N

物化性质

• 沸点：
  290.6±40.0 °C(Predicted)
• 密度：
  1.698±0.06 g/cm3(Predicted)
• 物理描述：
  Liquid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D-erythrofuranose 在 zeolite H-USY-6 作用下， 以 水 为溶剂， 反应 5.0h， 生成 D-赤藓酮糖
  参考文献：
  名称：

  [EN] ISOMERISATION OF C4-C6 ALDOSES WITH ZEOLITES
  [FR] ISOMÉRISATION D'ALDOSES EN C4-C6 AVEC DES ZÉOLITES

  摘要：

  本发明涉及将C4-C6醛糖异构化为它们对应的C4-C6酮糖。具体而言，该发明涉及在适当的溶剂存在下，在适当的升温条件下，将C4-C6醛糖在除铝以外没有任何金属的固体沸石催化剂上进行异构化。来自生物质前体的大量C6和C5醛糖，如葡萄糖和木糖，通过一步或两步过程在廉价的商业可获得的仅含铝作为催化剂中唯一金属的沸石催化剂上分别异构化为果糖和木糖醛。所得的酮糖被用作食品和/或啤酒行业的甜味剂，或者经处理以获得下游平台化学品，如乳酸、HMF、乙酰丁酸、糠醛、MMHB等。图7

  公开号：

  WO2014033311A1
• 作为产物：
  描述：

  3,4-di-O-formyl-D-erythrose 在 水 作用下， 以92%的产率得到D-erythrofuranose
  参考文献：
  名称：

  β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives

  摘要：

  The D-manno-configured N-anisylated beta-lactam 40, the beta-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene: from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the beta-lactam amino acid 43, besides its hydrolysis product 44. Reductive N-acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-beta-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-beta-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected beta-lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2380::aid-hlca2380>3.0.co;2-p

文献信息

• Conversion of Unprotected Aldose Sugars to Polyhydroxyalkyl and <i>C</i>-Glycosyl Furans via Zirconium Catalysis
  作者：Nima Ronaghi、David M. Fialho、Christopher W. Jones、Stefan France

  DOI：10.1021/acs.joc.0c02176

  日期：2020.12.4

  An efficient, zirconium-catalyzed conversion of unprotected aldose sugars with acetylacetone to polyhydroxyalkyl furans or C-glycosylfurans is reported. The furan products are formed in up to 93% yield using 5–10 mol % ZrCl4. Pentoses are readily converted at room temperature, while hexoses and their oligosaccharides require mild heating (i.e., 50 °C). Efficient conversions of glycolaldehyde, glyceraldehyde

  据报道，未保护的醛糖与乙酰丙酮的有效锆催化转化为聚羟烷基呋喃或C-糖基呋喃。使用5–10 mol％ZrCl 4可以高达93％的产率形成呋喃产物。戊糖在室温下易于转化，而己糖及其寡糖则需要适度加热（即50°C）。还证明了乙醇醛，甘油醛，赤藓糖，庚糖和葡萄糖胺的有效转化。该方法至少在以下方面之一超越了先前的路易斯酸催化方法中的每一种：（i）较低的催化剂负载量；（ii）降低反应温度；（iii）缩短反应时间；（iv）等摩尔底物化学计量；（v）扩大食糖范围；（vi）更高的选择性；（vii）使用富含地球的Zr催化剂。
• Kinetic behaviour and relative reactivities of some aldoses, amino sugars, and methylated sugars towards platinum(IV) in alkaline medium
  作者：Kalyan Kali Sen Gupta、Bilkis Ara Begum、Biswajit Pal

  DOI：10.1016/s0008-6215(98)00136-0

  日期：1998.6

  The kinetic behaviour and relative reactivities of some carbohydrates (aldoses, amino sugars and methylated sugars) towards platinum(IV) in alkaline medium have been investigated. The reactions are first order with respect to [substrate] and Pt IV . The rates increase with the increase in OH − . The reactions show pseudo-first-order dependence on OH − . The oxidation rates in alkaline medium follow the

  摘要研究了碱性介质中某些碳水化合物（醛糖，氨基糖和甲基化糖）对铂（IV）的动力学行为和相对反应性。对于[底物]和Pt IV，反应是一阶的。比率随着OH-的增加而增加。反应显示出对OH-的伪一阶依赖性。碱性介质中的氧化速率遵循三糖>四糖>戊糖>己糖的顺序。已经计算出反应的活化参数。已经提出了反应的机制。
• Deoxygenation of Biomass-Derived Feedstocks: Oxorhenium-Catalyzed Deoxydehydration of Sugars and Sugar Alcohols
  作者：Mika Shiramizu、F. Dean Toste

  DOI：10.1002/anie.201203877

  日期：2012.8.6

  important for the conversion of biomass into chemicals and fuels. The methyltrioxorhenium‐catalyzed deoxydehydration reaction was successfully applied to this purpose using another alcohol as solvent/reductant. The reaction was highly stereospecific, affording linear polyene products from C4–C6 sugar alcohols and aromatic compounds from C4–C6 sugars.

  将糖转变为油：糖部分的脱氧反应对于将生物质转化为化学物质和燃料非常重要。使用另一种醇作为溶剂/还原剂，成功地将甲基三氧合or催化的脱氧脱水反应应用于此目的。该反应是高度立体，得到线性多烯的产品选自C 4 -C 6糖醇和芳族化合物选自C 4 -C 6克的糖。
• 4-Isopropyl-2-oxazolin-5-one anion as masked umpoled synthon for both formyl and hydroxycarbonyl anions: Generation, reactivity and synthetic applications
  作者：Achille Barco、Simonetta Benetti、Carmela De Risi、Gian P Pollini、Giampiero Spalluto、Vinicio Zanirato

  DOI：10.1016/0040-4020(96)00143-3

  日期：1996.3

  formaldehyde. On the other hand, the same anion of 1 may act as a masked umpoled synthon for a hydroxycarbonyl anion since its aldol adducts with aldehydes underwent concomitant isomerization and ring cleavage under mild basic conditions producing dipeptides which could be hydrolyzed to give the corresponding carboxylic acids. Synthetic applications of this chemistry in the area of sugar, aminosugar and non-proteinogenic

  标题化合物的阴离子是在催化量的三乙胺存在下简单产生的，它与常见的亲电子烯烃和醛反应，分别得到中等或良好的迈克尔或醛醇加合物收率。在室温下对这些加合物进行轻度酸处理可掩盖醛的功能，使人们可以将1的阴离子视为甲醛的亲核酰化当量。另一方面，相同的阴离子1可以用作羟羰基阴离子的掩蔽的缩聚的合成酮，因为它的醛与醛的加合物在温和的碱性条件下进行异构化和开环裂解，生成二肽，可以水解得到相应的羧酸。讨论了该化学方法在糖，氨基糖和非蛋白氨基酸衍生物领域中的合成应用。
• PHOTOOXIDATION OF D-FRUCTOSE WITH IRON(III) CHLORIDE UNDER AEROBIC CONDITION
  作者：Koji Araki、Masato Sakuma、Shinsaku Shiraishi

  DOI：10.1246/cl.1983.665

  日期：1983.5.5

  d-Fructose is oxidatively degraded to d-erythrose with iron(III) chloride by photo-irradiation through Pyrex under aerobic as well as anaerobic condition. The reaction is suggested to proceed via formation of iron(III)-d-fructose complex and subsequent photo-redox process.

  在有氧和无氧条件下，通过Pyrex玻璃进行光照射，d-果糖可以在氯化铁(III)的作用下氧化降解生成d-赤藓糖。该反应被认为通过形成铁(III)-d-果糖络合物并随后进行光氧化还原过程进行。