scleropentaside A | 1360110-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: scleropentaside A
• 英文别名: furan-2-yl-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methanone
• CAS: 1360110-46-8
• 化学式: C₁₁H₁₄O₇
• 分子量: 258.228
• InChiKey: JDGRHJLOLKKFQC-YAOIVLIJSA-N

物化性质

• 沸点：
  517.7±50.0 °C(Predicted)
• 密度：
  1.547±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  scleropentaside A 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以14 mg的产率得到
  参考文献：
  名称：

  Unprecedented furan-2-carbonyl C-glycosides and phenolic diglycosides from Scleropyrum pentandrum

  摘要：

  Five unprecedented furan-2-carbonyl C-glycosides, scleropentasides A-E, and two phenolic diglycosides, 4-hydroxy-3-methoxybenzyl 4-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside and 2,6-dimethoxy-p-hydroquinone 1-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside, were isolated from leaves and twigs of Scleropyrum pentandrum together with potalioside B, luteolin 6-C-beta-D-glucopyranoside (isoorientin), apigenin 8-C-beta-D-glucopyranoside (vitexin), apigenin 6,8-di-C-beta-D-glucopyranoside (vicenin-2), apigenin 6-C-alpha-L-arabinopyranosyl-8-C-beta-D-glucopyranoside (isoschaftoside), apigenin 6-C-beta-D-glucopyranosyl-8-C-beta-D-xylopyranoside, adenosine and L-tryptophan. Structure elucidations of these compounds were based on analyses of chemical and spectroscopic data, including 1D and 2D NMR. In addition, the isolated compounds were evaluated for their radical scavenging activities using both DPPH and ORAC assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.11.001
• 作为产物：
  描述：

  (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 在 iron(III) chloride 、 双氧水 、 碘 、 叔丁基锂 、 sodium dodecyl-sulfate 作用下， 以 2-甲基四氢呋喃 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 4.17h， 生成 scleropentaside A
  参考文献：
  名称：

  β-选择性C-糖基化及其在巩膜戊糖苷A合成中的应用

  摘要：

  C-糖苷是在异头中心与糖苷配基具有C-C键的碳水化合物。由于它们对化学和酶水解的高度稳定性，这些化合物被广泛用作药物开发中的碳水化合物模拟物。在此，我们报告了茂盛的天然酰基的合成一般和专门β选择性方法Ç在scleropentaside天然产品系列首次发现糖苷结构基元。Corey–Seebach化合物反应是巩膜戊糖苷A及其类似物合成的关键步骤，仅在四个步骤中即可从未保护的碳水化合物开始，β-选择性构建异头C-C键。一锅法具有很高的原子效率，并且避免使用有毒的重金属。

  DOI：

  10.1002/anie.201900995

文献信息

• β-Selective One-Pot Synthesis of Acyl-C-Glycosides via Corey–Seebach Umpolung Reaction
  作者：G. Jacob Boehlich、Nina Schützenmeister

  DOI：10.1055/s-0039-1690158

  日期：2019.10

  C-Glycosides are commonly used as carbohydrate mimics in drug development due to their stability against enzymatic and chemical hydrolysis. In this Synpacts article we elaborate on our fast and efficient β-selective approach towards protected and unprotected acyl glycosides. Application of a Corey–Seebach umpolung reaction enables the exclusive formation of the β-anomer of aromatic acyl-C-glycosides in good to excellent yields.

  1 Introduction

  2 C-Glycosylation of Benzylated Glycosyl Donors

  3 C-Glycosylation of Silylated Glycosyl Donors

  4 Conclusion

  C-糖苷在药物开发中常被用作碳水化合物的模拟物，因为它们对酶促和化学水解具有稳定性。在这篇Synpacts文章中，我们详细介绍了我们快速高效的β-选择性方法，用于合成受保护和未受保护的酰基糖苷。应用Corey–Seebach反转反应能够专一性地形成芳香酰基-C-糖苷的β-异构体，并且产率良好到优秀。 1 引言 2 苄基化糖基供体的C-糖基化 3 硅基化糖基供体的C-糖基化 4 结论
• Cyanide-Free Synthesis of Glycosyl Carboxylic Acids and Application for the Synthesis of Scleropentaside A
  作者：Liang-Jing Zou、Qiang Pan、Cai-Yi Li、Ze-Ting Zhang、Xiao-Wei Zhang、Xiang-Guo Hu

  DOI：10.1021/acs.orglett.0c02949

  日期：2020.11.6

  We have developed a cyanide-free strategy for the synthesis of glycosyl carboxylic acids, which can provide 1,2-trans or 1,2-cis glycosyl carboxylic acids and is compatible with common protecting groups. The synthetic utility was demonstrated by the synthesis of 12 unreported glycosyl acids and the total synthesis of scleropentaside A.

  我们开发了一种用于合成糖基羧酸的无氰化物策略，它可以提供 1,2-反式或 1,2-顺式糖基羧酸，并且与常见的保护基团兼容。合成效用通过 12 种未报告的糖基酸的合成和 sclerpentaside A 的全合成得到证明。
• Synthesis of (non-classical) C-acyl-glycosides via Liebeskind–Srogl coupling: Scope, limitation, improved synthesis and antioxidant activity of scleropentaside A
  作者：Ze-Ting Zhang、Yue Ma、Nai-Li Fan、Xiang-Guo Hu

  DOI：10.1016/j.tet.2021.132255

  日期：2021.7
• Two New Galloyl Glucosides from the Leaves of Castanopsis fordii
  作者：Yong-Lin Huang、Ke-Di Yang、Zhang-Bin Liu、Ya-Feng Wang、Li Ge、Rui-Jie He、Jin-Lei Liu、Dian-Peng Li

  DOI：10.3987/com-17-s(t)5

  日期：——

  Two new galloyl glucosides, furan-2-carbonyl 6-C-beta-D-(6'-O-galloyl)glucopyranoside (I), grasshopper ketone 5-O-beta-D-(6'-O-galloyl)glucopyranoside (2), and one known compound 4-quinolone-2-carboxylic acid, were isolated from ethanol extract of the fresh leaves of Castanopsis fordii (Fagaceae). The chemical structures of these compounds were determined by one and two dimensional (1D and 2D)-NMR, liquid chromatography/time-of-flight/mass spectrometry (LC/TOF/MS), chemical evidence, and comparison with the literature.
• β‐Selective <i>C</i> ‐Glycosylation and its Application in the Synthesis of Scleropentaside A
  作者：G. Jacob Boehlich、Nina Schützenmeister

  DOI：10.1002/anie.201900995

  日期：2019.4

  C‐Glycosides are carbohydrates that bear a C−C bond to an aglycon at the anomeric center. Due to their high stability towards chemical and enzymatic hydrolysis, these compounds are widely used as carbohydrate mimics in drug development. Herein, we report a general and exclusively β‐selective method for the synthesis of a naturally abundant acyl‐C‐glycosidic structural motif first found in the scleropentaside

  C-糖苷是在异头中心与糖苷配基具有C-C键的碳水化合物。由于它们对化学和酶水解的高度稳定性，这些化合物被广泛用作药物开发中的碳水化合物模拟物。在此，我们报告了茂盛的天然酰基的合成一般和专门β选择性方法Ç在scleropentaside天然产品系列首次发现糖苷结构基元。Corey–Seebach化合物反应是巩膜戊糖苷A及其类似物合成的关键步骤，仅在四个步骤中即可从未保护的碳水化合物开始，β-选择性构建异头C-C键。一锅法具有很高的原子效率，并且避免使用有毒的重金属。