2,3,4,5,6-penta-O-acetyl-1-deoxy-1-(1,3-dimethyl-2,4,6-trioxo-1H,3H,5H-pyrimidin-5-ylidene)-D-glucitol | 89756-42-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,5,6-penta-O-acetyl-1-deoxy-1-(1,3-dimethyl-2,4,6-trioxo-1H,3H,5H-pyrimidin-5-ylidene)-D-glucitol
• CAS: 89756-42-3；89885-69-8；89885-70-1
• 化学式: C₂₂H₂₈N₂O₁₃
• 分子量: 528.47
• InChiKey: HBZZIEPGUQBFTM-WJFTUGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.75
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  189.19
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  5,5-二甲基-3-(4-甲基苯胺基)环己-2-烯-1-酮 、 2,3,4,5,6-penta-O-acetyl-1-deoxy-1-(1,3-dimethyl-2,4,6-trioxo-1H,3H,5H-pyrimidin-5-ylidene)-D-glucitol 以 二氯甲烷 为溶剂， 反应 72.0h， 以78%的产率得到(1'S,2'R,3'R,4'R)-5-(1',2',3',4',5'-penta-O-acetylpentane-1',2',3',4',5'-pentaolyl)-6-hydroxy-1,3,8,8-tetramethyl-9a-(4-methylanilino)-1,2,3,4,7,8,9,9a-octahydro-5H-chromeno[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Application of dimedone enamines as dienophiles: stereoselective synthesis of amino enols of fused uracils containing a sugar moiety by hetero-Diels–Alder reactions of barbituric acid 5-ylidene alditols with dimedone enamines

  摘要：

  Dimedone enamines were applied for the first time as new dienophiles in hetero-Diels-Alder reactions with inverse electron demand. Cycloadditions of barbituric acid 5-ylidene alditols with dimedone enamines were performed in dichloromethane at room temperature for 3 days and fused uracils-chromeno[2,3-d]pyrimidine-2,4-diones were obtained in good 73-87% yields. Only one enantiomerically pure stereoisomer was obtained in each studied cycloaddition. Analysis of H-1 NMR and 2D NMR spectra allowed for the determination that cycloadducts exist in solution as mixture of the neutral form and dipolar ion. The prepared fused uracils contain both amine and enol functional groups, so share amphiprotic properties and they are zwitterions in solid state. The new class of compounds-amino enols was synthesized, which similarly to amino acids exists as zwitterions. In obtained cycloadducts amino groups and sugar moieties are close each other and they both are in cis configuration and in axial position. It was also shown that different alkenes can be used as dienophiles towards barbituric acid 5-ylidene alditols, for example, styrene or 1-amino-2-thiocarbamoyi-cyclopent-1-ene. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.065
• 作为产物：
  描述：

  D-葡萄糖 在 sodium carbonate 、 zinc(II) chloride 作用下， 以 水 为溶剂， 反应 25.0h， 生成 2,3,4,5,6-penta-O-acetyl-1-deoxy-1-(1,3-dimethyl-2,4,6-trioxo-1H,3H,5H-pyrimidin-5-ylidene)-D-glucitol
  参考文献：
  名称：

  2,4,6-三氧嘧啶嘧啶-5-亚烷基糖醇在杂二戴尔斯-阿尔德反应和共轭迈克尔加成环合反应中合成含糖基吡喃并[2,3- d ]嘧啶的应用

  摘要：

  描述了一种方便有效的制备含糖部分的3，4-二氢-2 H-吡喃衍生物的方法。反应顺序为：未保护的糖和CH酸的Knoevenagel缩合，C-糖苷的乙酰化作用和杂Diels-Alder反应。在融合的尿嘧啶-具有糖部分的吡喃并[2,3- d ]嘧啶的合成中，将O-乙酰化的1,3-二甲基-2,4,6-三氧代嘧啶-5-亚甲基衍生物用作新的杂二烯。在室温下研究了无溶剂的O-乙酰化嘧啶-5-亚烷基醛醇的杂-狄尔斯-阿德环与烯醇醚和环状烯醇醚的加成反应。吡喃[2,3-]的新的对映体纯的顺式和反式非对映异构体d ]嘧啶和顺-顺，吡喃并[3的反式-非对映体顺式'，2'：5,6]吡喃并[2,3- d获得]与糖醇部分嘧啶。在室温下，相同的嘧啶5-亚烷基醛糖醇与丙二腈进行共轭迈克尔加成环化反应，得到具有糖基的吡喃并[2,3 - d ]嘧啶-6-腈的光学活性非对映异构体。

  DOI：

  10.1016/j.tet.2013.07.032

文献信息

• Facile preparation of C-glycosylbarbiturates and C-glycosylbarbituric acids
  作者：Martin Avalos Gonzalez、Jose L. Jimenez Requejo、Juan C. Palacios Albarran、Juan A. Gabis Perez

  DOI：10.1016/0008-6215(86)84005-8

  日期：1986.12

  method for the synthesis of pyrimidine C -nucleosides involves a one-step reaction of aldohexoses and aldopentoses with barbituric acids. Thus, 2-amino-2-deoxy- d -glucose was converted into 5-(2-amino-2-deoxy-β- d -glucopyranosyl)barbituric and 5-(2-amino-2-deoxy-β- d -glucopyranosyl)-1,3-dimethyl-barbituric acids. Likewise, d -glucose, d -galactose, d -mannose, d -xylose, d -ribose, and d -arabinose

  摘要合成嘧啶C-核苷的一般方法涉及醛糖己糖和醛糖戊糖与巴比妥酸的一步反应。因此，将2-氨基-2-脱氧-d-葡萄糖转化为5-（2-氨基-2-脱氧-β-d-吡喃葡萄糖基）巴比妥酸和5-（2-氨基-2-脱氧-β-d-葡萄糖。吡喃葡萄糖基）-1,3-二甲基-巴比妥酸。同样，将d-葡萄糖，d-半乳糖，d-甘露糖，d-木糖，d-核糖和d-阿拉伯糖转化为5-d-glycopyranosyl-1,3-二甲基-巴比妥酸钠（11–16;平均产量80％）。还获得具有α-d-阿拉伯吡喃糖基和β-d-吡喃半乳糖基结构的游离酸17和18。乙酰化11-18可以得到O-乙酰化的1,3-二甲基-2,4,6-三氧代-1 H，3 H，5 H-嘧啶-5-亚基-糖醇，尽管也获得了一些具有吡喃类结构的化合物。
• Perez, Juan A. Galbis; Gonzalez, Martin Avalos; Requejo, Jose L. Jimenez, Carbohydrate Research, 1983, vol. 124, p. C15 - C17
  作者：Perez, Juan A. Galbis、Gonzalez, Martin Avalos、Requejo, Jose L. Jimenez、Albarran, Juan C. Palacios

  DOI：——

  日期：——