methyl {4'-[3''-(methyl prop-2''(E)-enoate)]phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate | 866417-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl {4'-[3''-(methyl prop-2''(E)-enoate)]phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[(E)-3-methoxy-3-oxoprop-1-enyl]phenoxy]oxane-2-carboxylate
• CAS: 866417-47-2
• 化学式: C₂₃H₂₆O₁₂
• 分子量: 494.452
• InChiKey: KVAYXNCXOZCJCI-HIRIXVQTSA-N

物化性质

• 沸点：
  573.2±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、DCM、乙酸乙酯、

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl {4'-[3''-(methyl prop-2''(E)-enoate)]phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 在 lithium hydroxide 、 Amberlite IR₁₂₀ (H+) 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以70%的产率得到sodium {4'-[3''-(sodium prop-2''(E)-enoate)]phenyl β-D-glucopyranosid}uronate
  参考文献：
  名称：

  Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid

  摘要：

  This work describes our preliminary efforts towards the development of aryl glucuronides as potential probes for heparanase. During the course of these initial investigations, attempted glycosidation of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with 4-hydroxycinnamic acid gave a complex mixture of four different components. These were identified as the 1-cinnamyl glucuronate ester 13, the cinnamyl linked disaccharide 14, the glucuronate trichloroacetamide 15, and the glucuronyl alpha-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to optimise the formation of the alpha-fluoride 16. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.029
• 作为产物：
  描述：

  4-香豆酸 在 氯化亚砜 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 methyl {4'-[3''-(methyl prop-2''(E)-enoate)]phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate
  参考文献：
  名称：

  Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid

  摘要：

  This work describes our preliminary efforts towards the development of aryl glucuronides as potential probes for heparanase. During the course of these initial investigations, attempted glycosidation of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with 4-hydroxycinnamic acid gave a complex mixture of four different components. These were identified as the 1-cinnamyl glucuronate ester 13, the cinnamyl linked disaccharide 14, the glucuronate trichloroacetamide 15, and the glucuronyl alpha-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to optimise the formation of the alpha-fluoride 16. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.029

文献信息

• Synthesis of hydroxycinnamic acid glucuronides and investigation of their affinity for human serum albumin
  作者：Stéphanie Galland、Njara Rakotomanomana、Claire Dufour、Nathalie Mora、Olivier Dangles

  DOI：10.1039/b809965k

  日期：——

  Hydroxycinnamic acids (HCAs) are among the most abundant dietary polyphenols. Recent bioavailability studies have shown that HCAs enter the blood circulation mainly as glucuronides, which are thus most likely to express their potential health effects. In this work, an efficient synthesis of HCA O-arylglucuronides is developed. As for many xenobiotics, the resilience of HCA O-arylglucuronides in plasma and subsequent delivery to tissues could be governed by their binding to human serum albumin (HSA). Hence, the affinity of HCA O-arylglucuronides for HSA and its possible binding site were investigated by fluorescence spectroscopy. HCA O-arylglucuronides turn out to be moderate HSA ligands (K in the range 1–4 × 104 M−1) that bind HSA in sub-domain IIA, competitively or noncompetitively with other sub-domain IIA ligands such as dansylamide and the flavonol quercetin.

  羟基肉桂酸（HCA）是最丰富的膳食多酚之一。最近的生物利用率研究表明，HCA 主要以葡糖醛酸的形式进入血液循环，因此最有可能体现其潜在的健康功效。本研究开发了一种高效合成 HCA O-芳基葡萄糖醛酸的方法。与许多异种生物一样，HCA O-芳基葡萄糖醛酸在血浆中的持久性以及随后向组织的输送可能受其与人血清白蛋白（HSA）结合的影响。因此，我们通过荧光光谱法研究了 HCA O-芳基葡萄糖醛酸与 HSA 的亲和力及其可能的结合位点。结果表明，HCA O-芳基葡萄糖醛酸是一种温和的 HSA 配体（K 值范围为 1-4 × 104 M-1），可与其他亚域 IIA 配体（如丹参酰胺和黄酮醇槲皮素）竞争性或非竞争性地在亚域 IIA 与 HSA 结合。