2,4-di-C-(hydroxymethyl)-3-pentulose | 74042-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-di-C-(hydroxymethyl)-3-pentulose
• 英文别名: 2,4-bis(hydroxymethyl)-3-pentulose；1,2,4,5-Tetrahydroxy-2,4-bis(hydroxymethyl)pentan-3-one
• CAS: 74042-85-6
• 化学式: C₇H₁₄O₇
• 分子量: 210.184
• InChiKey: AOBFYPUERRIKRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  138
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4-di-C-(hydroxymethyl)-3-pentulose 在 sodium tetrahydroborate 作用下， 生成 2,4-bis(hydroxymethyl)-1,2,3,4,5-pentanepantaol
  参考文献：
  名称：

  A selective synthesis of 2,4-di-C-(hydroxymethyl)-3-pentulose in the formose reaction

  摘要：

  DOI：

  10.1016/s0008-6215(00)85330-6
• 作为产物：
  描述：

  1,2:4,5-di-O-isopropylidene-D-arabinitol 在 重铬酸吡啶 、 乙酸酐 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2,4-di-C-(hydroxymethyl)-3-pentulose
  参考文献：
  名称：

  Synthesis of Carbohydrates in Mineral-Guided Prebiotic Cycles

  摘要：

  One present obstacle to the "RNA-first" model for the origin of life is an inability to generate reasonable "hands off" scenarios for the formation of carbohydrates under conditions where they might have survived for reasonable times once formed. Such scenarios would be especially compelling if they deliver pent(ul)oses, five-carbon sugars found in terran genetics, and exclude other carbohydrates (e.g., aldotetroses) that may also be able to function in genetic systems. Here, we provide detailed chemical analyses of carbohydrate premetabolisin, showing how borate, molybdate, and calcium minerals guide the formation of tetroses (C(4)H(8)O(4)), heptoses (C(7)H(14),O(7)), and pentoses (C(5)H(10)O(5)), including the ribose found in RNA, in "hands off" experiments, starting with formaldehyde and glycoaldehyde. These results show that pent(ul)oses would almost certainly have formed as stable borate complexes on the surface of an early Earth beneath a humid CO(2) atmosphere suffering electrical discharge. While aldotetroses form extremely stable complexes with borate, they are not accessible by pathways plausible under the most likely early Earth scenarios. The stabilization by borate is not, however, absolute. Over longer times, material is expected to have passed from borate-bound pent(ul)oses to a branched heptulose, which is susceptible to Cannizzaro reduction to give dead end products. We show how this fate might be avoided using molybdate-catalyzed rearrangement of a branched pentose that is central to borate-moderated cycles that fix carbon from formaldehyde. Our emerging understanding of the nature of the early Earth, including the presence of hydrated rocks undergoing subduction to form felsic magmas in the early Hadean eon, may have made borate and molydate species available to prebiotic chemistry, despite the overall "reduced" state of the planet.

  DOI：

  10.1021/ja201769f

文献信息

• Formose Reactions. XXVIII. Selective Formation of 2,4-Bis(hydroxymethyl)-3-pentulose in<i>N</i>,<i>N</i>-Dimethylformamide–Water Mixed Solvent
  作者：Yoshihiro Shigemasa、Takaaki Ueda、Hiroyuki Saimoto

  DOI：10.1246/bcsj.63.389

  日期：1990.2

  Dihydroxyacetone, DL-glycero-tetrulose, and 2,4-bis(hydroxymethyl)-3-pentulose (2,4-BH-3-P) were favorably formed in a formose reaction by choosing a suitable ratio of water to N,N-dimethylformamide used as solvent or a suitable [thiamine·HCl]/[HCHO] ratio. The formose reaction was strongly affected by the concentration of formaldehyde in the water layer. Under the reaction conditions studied, thiamine

  通过选择合适的水与 N,N 的比例，二羟基丙酮、DL-甘油四糖和 2,4-双(羟甲基)-3-戊酮糖 (2,4-BH-3-P) 在甲糖反应中有利地形成-二甲基甲酰胺用作溶剂或合适的[硫胺素·HCl]/[HCHO]比率。甲糖反应受水层中甲醛浓度的强烈影响。在研究的反应条件下，硫胺迅速分解。从反应混合物中分离出 2,4-BH-3-P，并通过 MS、IR 和 NMR 技术进行表征。还提出了形成 2,4-BH-3-P 的途径。
• SHIGEMASA, YOSHIHIRO;UEDA, TAKAAKI;SAIMOTO, HIROYUKI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 389-394
  作者：SHIGEMASA, YOSHIHIRO、UEDA, TAKAAKI、SAIMOTO, HIROYUKI

  DOI：——

  日期：——