1-(2,2,2-三氟-N-苯基乙亚氨酸酯)-D-吡喃葡萄糖醛酸甲酯2,3,4-三乙酸酯 | 869996-05-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2,2,2-三氟-N-苯基乙亚氨酸酯)-D-吡喃葡萄糖醛酸甲酯2,3,4-三乙酸酯
• 中文别名: 1-(2,2,2-三氟-N-苯基亚胺酯)-2,3,4-三-O-乙酰基-D-葡萄糖醛酸甲酯
• 英文名称: methyl (2,3,4-tri-O-acetyl-D-glucopyranosyl (N-phenyl)trifluoroacetimidate)uronate
• 英文别名: methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl N-phenyl-2,2,2-trifluoroacetimidate；O-(methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl)-N-phenyl-2,2,2-trifluoroacetimidate；2,3,4-tri-O-acetyl-D-methylglucuronopyranosyl(N-phenyl)-2,2,2-trifluoroacetimidate；1-(2,2,2-Trifluoro-N-phenylethanimidate)-D-glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate；methyl (2S,3S,4S,5R)-3,4,5-triacetyloxy-6-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxane-2-carboxylate
• CAS: 869996-05-4
• 化学式: C₂₁H₂₂F₃NO₁₀
• 分子量: 505.402
• InChiKey: YIVKGVGMDKWGAE-VPQNOXPISA-N

物化性质

• 熔点：
  95-97°C
• 沸点：
  480.2±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-(2,2,2-三氟-N-苯基乙亚氨酸酯)-D-吡喃葡萄糖醛酸甲酯2,3,4-三乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以69%的产率得到(3R,4S,5S,6S)-2-(4-formyl-2-methoxyphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  First Chemical Synthesis and in Vitro Characterization of the Potential Human Metabolites 5-O-Feruloylquinic Acid 4′-Sulfate and 4′-O-Glucuronide

  摘要：

  Feruloylquinic acids are a major class of biologically active phenolic antioxidants in coffee beans, but their metabolic fate is poorly understood. The present study investigated the phase II metabolism of feruloylquinic adds with selected human sulfotransferases (SULT1A1 and SULT1E1) and uridine 5'-diphosphoglucuronosyltransferases (UGT1A1 and UGT1A9). For unequivocal metabolite identification, the chemical synthesis of two potential human metabolites of 5-O-feruloylquinic acid, the 4'-sulfated and 4'-O-glucuronidated conjugates, has been performed for the first time. Following incubation with human SULT1A1 or SULT1E1, formation of 5-O-feruloylquinic acid 4'-O-sulfate was confirmed by matching its HPLC and MS data with those of the authentic standard. On the other hand, no glucuronide conjugates were detected after incubation with human uridine 5'-diphosphoglucuronosyltransferases. These results suggest that sulfation can take place on the ferulic acid moiety of feruloylquinic acids and may be a major metabolic pathway for feruloylquinic acids in humans.

  DOI：

  10.1021/jf200272m
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 、 2,2,2-三氟-N-苯基亚氨代乙酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到1-(2,2,2-三氟-N-苯基乙亚氨酸酯)-D-吡喃葡萄糖醛酸甲酯2,3,4-三乙酸酯
  参考文献：
  名称：

  Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities

  摘要：

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

  DOI：

  10.1021/jo051384k

文献信息

• Epicatechin B-Ring Conjugates: First Enantioselective Synthesis and Evidence for Their Occurrence in Human Biological Fluids
  作者：Fedor Romanov-Michailidis、Florian Viton、René Fumeaux、Antoine Lévèques、Lucas Actis-Goretta、Maarit Rein、Gary Williamson、Denis Barron

  DOI：10.1021/ol3016463

  日期：2012.8.3

  Herein, the first enantioselective total synthesis of a number of biologically relevant (−)-epicatechin conjugates is described. The success of this synthesis relied on (i) optimized conditions for the stereospecific cyclization step leading to the catechin C ring; on (ii) efficient conjugation reactions; and on (iii) optimized deprotection sequences. These standard compounds have been subsequently

  在此，描述了许多生物学上相关的（-）-表儿茶素结合物的第一对映选择性全合成。该合成的成功取决于（i）导致儿茶素C环的立体有择环化步骤的最佳条件；（ii）有效的共轭反应；（iii）优化的脱保护序列。随后，这些标准化合物首次用于阐明在（-）-表儿茶素吸收后存在于四种不同人类生物液中的（-）-表儿茶素结合物的模式。
• First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption
  作者：René Fumeaux、Candice Menozzi-Smarrito、Angelique Stalmach、Caroline Munari、Karin Kraehenbuehl、Heike Steiling、Alan Crozier、Gary Williamson、Denis Barron

  DOI：10.1039/c0ob00137f

  日期：——

  A systematic investigation of the human metabolism of hydroxycinnamic acid conjugates was carried out. A set of 24 potential human metabolites of coffee polyphenols has been chemically prepared, and used as analytical standards for unequivocal identifications. These included glucuronide conjugates and sulfate esters of caffeic, ferulic, isoferulic, m-coumaric and p-coumaric acids as well as their dihydro derivatives. A particular focus has been made on caffeic and 3,4-dihydroxyphenylpropionic acid derivatives, especially the sulfate conjugates, for which regioselective preparation was particularly challenging, and have so far never been identified as human metabolites. Ten out of the 24 synthesized conjugates have been identified in human plasma and/or urine after coffee consumption. A number of these conjugates were synthesized, characterized and detected as hydroxycinnamic acid metabolites for the first time. This was the case of dihydroisoferulic acid 3′-O-glucuronide, caffeic acid 3′-sulfate, as well as the sulfate and glucuronide derivatives of 3,4-dihydroxyphenylpropionic acid.

  对人类对羟基肉桂酸缀合物的代谢进行了系统研究。化学合成了一组24种可能的人类咖啡多酚代谢产物，作为明确鉴定的分析标准。这些包括咖啡酸、阿魏酸、异阿魏酸、m-香豆酸和p-香豆酸的葡萄糖苷缀合物和硫酸酯，以及它们的二氢衍生物。特别关注于咖啡酸和3,4-二羟基苯丙酸衍生物，尤其是硫酸缀合物，其区域选择性合成特别具有挑战性，迄今为止从未被确认作为人类代谢产物。在咖啡消费后，从24种合成的缀合物中，10种已在人体血浆和/或尿液中被确认检测到。这些缀合物中的一些首次被合成、表征并检测为羟基肉桂酸代谢产物。包括3′-O-葡萄糖醛酸二氢异阿魏酸、3′-硫酸咖啡酸，以及3,4-二羟基苯丙酸的硫酸和葡萄糖醛酸衍生物。
• First <i>O</i>-Glycosylation of Hydroxamic Acids
  作者：Mickaël Thomas、Jean-Pierre Gesson、Sébastien Papot

  DOI：10.1021/jo0701839

  日期：2007.5.1

  The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 angstrom molecular sieves in dichloromethane. Under such conditions, a wide range of new glycosyl donors including glucosyl, galactosyl, mannosyl, glucuronyl, and ribosyl hydroxamates were prepared in good to high yields. This procedure appears to be an advantageous alternative for the synthesis of glycosyl hydroxamates of biological interest.