β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate | 16684-19-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate
• 英文别名: ursolic acid 28-O-β-D-glucopyranosyl ester；ursolic acid 28-O-β-D-glucopyranoside；ursolic acid β-D-glucopyranosyl ester；ursolic acid 28-O-(β-D-glucopyranosyl) ester；Ursolic acid-28-O-I(2)-D-glucopyranosyl ester；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 16684-19-8
• 化学式: C₃₆H₅₈O₈
• 分子量: 618.852
• InChiKey: BVBAYRAWOPYPGO-YDMYVTAASA-N

物化性质

• 熔点：
  192 °C
• 沸点：
  699.8±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  熊果酸 在 甲醇 、 水 、 甲基三辛基氯化铵 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate
  参考文献：
  名称：

  在相转移条件下酸的糖基化。皂苷的部分合成

  摘要：

  通过各种羧酸与乙酰溴糖的反应，可以高产率制备β-D-糖基酯。反应在相转移条件下使用碳酸钾。脱乙酰基得到β-D-糖基羧酸盐。

  DOI：

  10.1016/0040-4039(94)88088-3

文献信息

• Naturally Occurring Pentacyclic Triterpenes as Inhibitors of Glycogen Phosphorylase: Synthesis, Structure−Activity Relationships, and X-ray Crystallographic Studies
  作者：Xiaoan Wen、Hongbin Sun、Jun Liu、Keguang Cheng、Pu Zhang、Liying Zhang、Jia Hao、Luyong Zhang、Peizhou Ni、Spyros E. Zographos、Demetres D. Leonidas、Kyra-Melinda Alexacou、Thanasis Gimisis、Joseph M. Hayes、Nikos G. Oikonomakos

  DOI：10.1021/jm8000949

  日期：2008.6.1

  Twenty-five naturally occurring pentacyclic triterpenes, 15 of which were synthesized in this study, were biologically evaluated as inhibitors of rabbit muscle glycogen phosphorylase a (GPa). From SAR studies, the presence of a sugar moiety in triterpene saponins resulted in a markedly decreased activity ( 7, 18- 20) or no activity ( 21, 22). These saponins, however, might find their value as potential

  二十五个天然存在的五环三萜，在本研究中合成了十五个，被生物评估为兔肌肉糖原磷酸化酶α（GPa）的抑制剂。根据SAR研究，三萜皂苷中糖部分的存在导致活性显着降低（7、18-20）或无活性（21、22）。但是，这些皂苷可能具有潜在的天然前药价值，它们的水溶性比其相应的糖苷配基要高得多。为了阐明GP抑制的机制，我们确定了GPb-亚硫酸和GPb-山梨酸复合物的晶体结构。X射线分析表明，抑制剂在生理活化剂AMP结合的变构活化剂位点结合。
• Base‐Promoted Glycosylation Allows Protecting Group‐Free and Stereoselective <i>O</i>‐Glycosylation of Carboxylic Acids**
  作者：Hao Zuo、Chen Zhang、Yang Zhang、Dawen Niu

  DOI：10.1002/anie.202309887

  日期：2023.10.16

  Here we report a simple and general method to achieve fully unprotected, stereoselective glycosylation of carboxylic acids, employing bench‐stable allyl glycosyl sulfones as donors. Running the glycosylation reaction under basic conditions was crucial for the efficiencies and selectivities. Both the donor activation stage and the glycosidic bond forming stage of the process are compatible with free hydroxyl groups, thereby allowing for the use of fully unprotected glycosyl donors. This transformation is stereoconvergent, occurs under mild and metal‐free conditions at ambient temperature with visible light (455 nm) irradiation, and displays remarkable scope with respect to both reaction partners. Many natural products and commercial drugs, including an acid derived from the complex anticancer agent taxol, were efficiently glycosylated. Experimental studies provide insights into the origin of the stereochemical outcome.

  摘要我们在此报告了一种简单而通用的方法，该方法采用台式稳定的烯丙基糖基砜作为给体，实现了羧酸的完全无保护、立体选择性糖基化。在碱性条件下进行糖基化反应对效率和选择性至关重要。该过程的供体活化阶段和糖苷键形成阶段都与游离羟基兼容，因此可以使用完全无保护的糖基供体。这种转化具有立体转换性，在环境温度和可见光（455 纳米）照射下，在温和、无金属的条件下进行，而且对两个反应伙伴都有显著的影响。许多天然产物和商业药物，包括从复合抗癌剂紫杉醇中提取的一种酸，都被有效地糖基化了。实验研究为了解立体化学结果的起源提供了见解。
• Glycosylation of acids under phase transfer conditions. Partial synthesis of saponins
  作者：Christophe Bliard、Georges Massiot、Serge Nazabadioko

  DOI：10.1016/0040-4039(94)88088-3

  日期：1994.8

  β-D-glycosyl esters are prepared in high yields by reaction of various carboxylic acids and acetobromosugars. The reaction uses potassium carbonate under phase tranfer conditions. Deacetylation affords the β-D-glycosyl carboxylates.

  通过各种羧酸与乙酰溴糖的反应，可以高产率制备β-D-糖基酯。反应在相转移条件下使用碳酸钾。脱乙酰基得到β-D-糖基羧酸盐。