5,6-O-isopropylidene-2-O-methyl-L-ascorbic acid | 87804-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-O-isopropylidene-2-O-methyl-L-ascorbic acid
• 英文别名: (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-4-methoxy-2H-furan-5-one
• CAS: 87804-25-9
• 化学式: C₁₀H₁₄O₆
• 分子量: 230.218
• InChiKey: LQRRGESBACGIAF-CAHLUQPWSA-N

物化性质

• 沸点：
  394.1±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-O-isopropylidene-2-O-methyl-L-ascorbic acid 在 氧气 、 rose bengal 作用下， 以 丙酮 为溶剂， 生成 (R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroperoxy-3-methoxy-furan-2,4-dione
  参考文献：
  名称：

  Photooxygenation of ascorbic acid derivatives and model compounds

  摘要：

  DOI：

  10.1021/ja00187a047
• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 四丁基氟化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 5,6-O-isopropylidene-2-O-methyl-L-ascorbic acid
  参考文献：
  名称：

  One-Pot 2-O-Alkylation of l-Ascorbic Acid

  摘要：

  One-pot 2-O-alkylation of L-ascorbic acid involving an in situ 3-O-silylation and desilylation sequence was investigated. Initially the 3-OH group was masked with a t-butyldimethylsilyl (TBDMS) group followed by alkylation of the 2-OH group. Removal of the TBDMS group using 20% sulfuric acid also resulted in hydrolysis of the 5,6-O-isopropylidene to give 2-O-alkyl derivatives of L-ascorbic acid. Selective removal of the 3-O-TBDMS with tetrabutylammonium fluoride (TBAF) gave 5,6-O-isopropylidene-2-O-alkyl derivatives of L-ascorbic acid in good overall yields. Through the application of this protocol, 5,6-O-isopropylidene 2-O-alkyl derivatives of L-ascorbic acid as well as 2-O-alkyl derivatives of L-ascorbic acid may be easily accessed.

  DOI：

  10.1055/s-0033-1338858

文献信息

• Rational Approach to Selective and Direct 2-<i>O</i>-Alkylation of 5,6-<i>O</i>-Isopropylidine-<scp>l</scp>-ascorbic Acid
  作者：Ayodele O. Olabisi、Kandatege Wimalasena

  DOI：10.1021/jo049319i

  日期：2004.10.1

  derivatives of l-ascorbic acid have been shown to possess antioxidant, antitumor, and immunostimulant activities. The antioxidant and redox properties of l-ascorbic acid are closely associated with the electron-rich 2,3-enediol moiety of the molecule, and therefore, selective functionalization of the 2- and 3-OH groups is essential for the detailed structure−activity studies. Reactions of 5- and 6-OH-protected

  1-抗坏血酸是一种广泛的自由基清除剂，广泛分布在需氧生物中，在保护细胞成分免受自由基和氧化剂的氧化损伤中起着核心作用。它也可作为生理还原剂，用于儿茶酚胺神经递质，酰胺化肽激素和胶原生物合成途径中的关键酶促转化。已显示1-抗坏血酸的简单衍生物具有抗氧化剂，抗肿瘤和免疫刺激活性。l的抗氧化和氧化还原特性-抗坏血酸与分子的富含电子的2,3-烯二醇部分紧密相关，因此，2-和3-OH基团的选择性官能化对于详细的结构活性研究至关重要。5-和6-OH-保护的抗坏血酸与亲电子试剂的反应由于C-3-OH的高亲核性，仅在温和的碱性条件下产生相应的3- O-烷基化产物。基于密度泛函理论（B3LYP）电子密度计算，我们设计了一种新颖的通用方法来对抗坏血酸的2-OH基团进行直接烷基化，具有完全的区域选择性和化学选择性。我们还对两个互补的2 - O-乙酰-3- O进行了完整的光谱分析-烷基-和2 - O-烷基-3-
• C2/C3 alkynylation of <scp>l</scp>-ascorbic acid by Sonogashira coupling and efficient access to some potent and highly selective novel anticancer agents
  作者：Santosh Rangnath Deshmukh、Shankar Ramchandra Thopate

  DOI：10.1039/c8nj04477e

  日期：——

  exhibited superior potency against human MCF7, A549 and HT29 cancer cell lines. Compound 7k showed 2.7, 16.6 and 6.2 fold more potency against MCF7, A549 and HT29 cell lines, respectively, compared to doxorubicin and 643 fold more potency compared to AsA against the MCF7 cancer cell line. Notably, it showed 25 fold less cytotoxicity towards the normal human umbilical vein endothelial cell (HUVEC) line as

  天然产物是开发新药的生物活性化合物的宝贵来源。本文中，我们报道了通过Sonogashira交叉偶联反应以中等至良好的产率合成L-抗坏血酸（AsA）的新型C2 / C3炔基衍生物的要求不高的合成方法。所有新的衍生物均显示出对人MCF7，A549和HT29癌细胞系的优越效力。复合7k分别显示出与阿霉素相比，对MCF7，A549和HT29细胞系的效力分别高出2.7、16.6和6.2倍，而与AsA相比，对MCF7癌细胞系的效力高出643倍。值得注意的是，与阿霉素抗癌药物相比，它对正常人脐静脉内皮细胞（HUVEC）的细胞毒性降低了25倍。令人愉快的是，与人正常细胞相比，它对人癌细胞的细胞毒性高333倍。流式细胞术研究表明，化合物4h和7k通过凋亡将A549细胞阻滞在G0 / G1期。此外，这些化合物具有很大的潜力被开发为有前途的抗癌药。
• Reaction of Ascorbic Acid with Aliphatic Amines
  作者：Monika Pischetsrieder、Bernd Larisch、Ursula Mueller、Theodor Severin

  DOI：10.1021/jf00060a002

  日期：1995.12

  Ascorbic acid (1) reacts with propylamine or alpha-N-acetyllysine to afford N-substituted 3-deoxy-3-aminoascorbic acid of general structure 3.
• SINGLE-COMPONENT ADHESIVE COMPOSITIONS
  申请人：Ohio State Innovation Foundation

  公开号：US20220135842A1

  公开（公告）日：2022-05-05

  Disclosed are single component, stimuli-responsive adhesives that cure in response to an applied stimulus, including single component moisture-curable adhesives (e.g., moisture-curable (meth)acrylate/polyurethane hybrid adhesives). These adhesive compositions can combine the non-toxic, high strength properties of (meth)acrylate adhesives with the bonding characteristics of polyurethanes. The compositions described herein employ imitator systems which trigger polymerization/curing of the adhesive composition in response to a stimulus, such as ambient moisture, mild heat, and/or by physical stress. These strategies eliminate the need for mixing or an external energy stimulus to initiate curing. In this way, the benefits of polyurethane adhesive chemistry can be brought to the consumer market, in a system that is readily usable by the average individual.
• [EN] SINGLE-COMPONENT ADHESIVE COMPOSITIONS<br/>[FR] COMPOSITIONS ADHÉSIVES À COMPOSANT UNIQUE
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2020168201A1

  公开（公告）日：2020-08-20

  Disclosed are single component, stimuli-responsive adhesives that cure in response to an applied stimulus, including single component moisture-curable adhesives (e.g., moisture-curable (meth)acrylate/polyurethane hybrid adhesives). These adhesive compositions can combine the non-toxic, high strength properties of (meth)acrylate adhesives with the bonding characteristics of polyurethanes. The compositions described herein employ imitator systems which trigger polymerization/curing of the adhesive composition in response to a stimulus, such as ambient moisture, mild heat, and/or by physical stress. These strategies eliminate the need for mixing or an external energy stimulus to initiate curing. In this way, the benefits of polyurethane adhesive chemistry can be brought to the consumer market, in a system that is readily usable by the average individual.