(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1332833-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1332833-26-7
• 化学式: C₅₇H₅₂O₁₆
• 分子量: 993.03
• InChiKey: LWDOQOAZKCUPOM-LQMNUCAHSA-N

物化性质

• 沸点：
  1004.8±65.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.24
• 重原子数：
  73.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  190.79
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 8.0h， 生成 异槲皮苷
  参考文献：
  名称：

  Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

  摘要：

  4'-O-beta-D-Glucopyranosyl-quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-beta-D-glucopyranoside (1), quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.062
• 作为产物：
  描述：

  在 盐酸 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

  摘要：

  4'-O-beta-D-Glucopyranosyl-quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-beta-D-glucopyranoside (1), quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.062

文献信息

• Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement
  作者：Jiagen Li、Ming Wang、Xuefeng Jiang

  DOI：10.1021/acs.orglett.1c03302

  日期：2021.12.3

  palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside

  立体选择性糖基化在碳水化合物化学中具有挑战性。在此，通过钯催化的烯丙基重排对糖醛进行立体选择性硫代糖基化，可在 α-异构体硫糖苷上产生各种取代基。通过硫代硫酸盐与衍生自葡萄糖、阿拉伯糖、半乳糖和鼠李糖的糖苷的组合，获得了两个综合系列的芳基和苄基硫糖苷。此外，薯蓣基 α-l-鼠李糖苷和异槲皮苷分别通过 α-亚砜-鼠李糖苷和 α-亚砜-葡萄糖苷的立体特异性 [2,3]-σ 重排实现了选择性。
• An expeditious synthesis of quercetin 3-O-β-d-glucuronide from rutin
  作者：Mohammed Kajjout、Rajae Zemmouri、Christian Rolando

  DOI：10.1016/j.tetlet.2011.06.108

  日期：2011.9

  We report the synthesis of the major human metabolite of quercetin, quercetin 3-O-β-d-glucuronide, from rutin (quercetin-3-rutinoside), which is commercially available at low cost. This straightforward synthesis is based on the key intermediate 3′,4′,5,7-tetra-O-benzyl-quercetin which is obtained in only two steps by the total benzylation of rutin followed by acid hydrolysis of the rutinoside residue

  我们报道了槲皮素的主要人类代谢产物，槲皮素3- O- β- d-葡萄糖苷酸的合成，得自芦丁（槲皮素-3-芸香糖苷），其价格低廉。这种简单的合成是基于关键中间体3'，4'，5,7-四-O-苄基-槲皮素，该步骤仅通过两步进行，即芦丁的总苄基化，然后通过芸苔苷残基的酸水解即可获得。1-溴-3,4,6-四-O-乙酰基-α- d对游离3羟基的糖基化作用-吡喃葡糖苷产生被保护的葡糖苷。TEMPO介导的脱保护的葡糖苷上伯醇的氧化使人们能够接触到苄基化的葡糖醛酸苷。通过H 2（10％Pd / C）除去保护槲皮素羟基的苄基产生槲皮素3- O- β- d-葡糖醛酸苷。
• Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK
  作者：Kosei Yamauchi、Tohru Mitsunaga、Mizuho Inagaki、Tohru Suzuki

  DOI：10.1016/j.bmc.2014.04.053

  日期：2014.7

  In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3',4',7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression. (C) 2014 Elsevier Ltd. All rights reserved.
• Development of flavonoid probes and the binding mode of the target protein and quercetin derivatives
  作者：Ayaka Tsuchiya、Miho Kobayashi、Yuji O. Kamatari、Tohru Mitsunaga、Kosei Yamauchi

  DOI：10.1016/j.bmc.2022.116854

  日期：2022.8