2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl trichloroacetimidate-¹C₄ | 213268-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl trichloroacetimidate-¹C₄
• 英文别名: 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl trichloroacetimidate；arabinosyl trichloroacetimidate；2,3,4-tri-O-benzoyl-β-D-xylopyranosyl tricholoroacetimidate；[(3S,4S,5R,6S)-4,5-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 213268-21-4
• 化学式: C₂₈H₂₂Cl₃NO₈
• 分子量: 606.844
• InChiKey: CTJJXLYHZINRRA-IFOBJOEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl trichloroacetimidate-¹C₄ 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  齐墩果糖二糖衍生物的合成

  摘要：

  摘要齐墩果酸1广泛存在于食品，药材等植物中，并具有许多诱人的生物学活性。最近，据报道一些齐墩果酸衍生物具有有趣的抗肿瘤活性。在此，利用药物设计的结合原理，通过偶联αL-鼠李糖基-（1→2）-αL-阿拉伯吡喃糖基二糖部分，设计合成了OA二糖17，其已被证明是具有强抗肿瘤活性的独特糖序列，并被修饰。在C-17上带有腈的OA。

  DOI：

  10.1016/j.cclet.2012.01.022
• 作为产物：
  描述：

  三氯乙腈 、 2,3,4-tri-O-benzoyl-L-arabinopyranose 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl trichloroacetimidate-¹C₄
  参考文献：
  名称：

  Synthesis of two natural betulinic acid saponins containing α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranose and their analogues

  摘要：

  A concise synthesis of naturally occurring betulinic acid saponins bearing an alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside moiety at the C-3 position is described. Betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[ -D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside isolated from Pulsatilla koreana and 28-O-beta-D-glucopyranosyl betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-a-L-arabinopyranoside isolated from Schefflera rotundifolia were easily synthesized for the first time using a stepwise glycosidation approach. The overall syntheses involved eight linear steps starting from allyl betulinate and commercially available L-arabinose, L-rhamnose and D-glucose. The syntheses of betulin and betulinic acid O-glycoside analogues containing an alpha-L-arabinose moiety are also reported. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.029

文献信息

• Synthesis ofα-Hederin,δ-Hederin, and Related Triterpenoid Saponins
  作者：Karen Plé、Martin Chwalek、Laurence Voutquenne-Nazabadioko

  DOI：10.1002/ejoc.200300723

  日期：2004.4

  osyl]hederagenin, 1), δ-hederin (3-O-(α-L-arabinopyranosyl)hederagenin, 3), and three related triterpenoid saponins is described as part of a study of the structure−activity relationships between triterpenoid saponins and hemolytic activity. 4-Methoxybenzyl α-L-arabinopyranoside (11) was synthesized first and then used to prepare the different arabinose acceptors. Glycosylation between the acceptors

  α-hederin (3-O-[α-L-rhamnopyranosyl-(1⇄2)-α-L-arabinopyranosyl]hederagenin, 1), δ-hederin (3-O-(α-L-arabinopyranosyl)的合成hederagenin, 3) 和三种相关的三萜皂苷被描述为三萜皂苷与溶血活性之间构效关系研究的一部分。首先合成 4-甲氧基苄基 α-L-阿拉伯吡喃糖苷 (11)，然后用于制备不同的阿拉伯糖受体。受体和 2,3,4-三-O-苯甲酰基-α-L-吡喃鼠李糖基三氯乙酰亚胺酯 (20) 之间的糖基化以极好的收率进行，得到所需的二糖。二糖的三氯乙酰亚胺衍生物与烯丙基-或甲基常春藤苷配伍以高产率得到受保护的皂苷。然后在脱保护后以良好至中等的产率获得皂苷及其相应的甲酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
• Synthesis of Some Phenylpropanoid Glycosides (PPGs) and Their Acetylcholinesterase/Xanthine Oxidase Inhibitory Activities
  作者：Xiao-Dong Li、Shuai-Tao Kang、Guo-Yu Li、Xian Li、Jin-Hui Wang

  DOI：10.3390/molecules16053580

  日期：——

  In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.

  在这项研究中，设计和合成了三类苯丙素糖苷（PPGs），以从红景天中分离的PPGs作为先导化合物。同时测试了它们对乙酰胆碱酯酶（AChE）和黄嘌呤氧化酶（XOD）的抑制能力。部分合成PPGs表现出了优异的酶抑制能力。
• Synthesis of water soluble glycosides of pentacyclic dihydroxytriterpene carboxylic acids as inhibitors of α-glucosidase
  作者：Jiancong Xu、Xuliang Nie、Yanping Hong、Yan Jiang、Guoqiang Wu、Xiaoli Yin、Chunrong Wang、Xiaoqiang Wang

  DOI：10.1016/j.carres.2016.02.009

  日期：2016.4

  including (1)H NMR, (13)C NMR and HRMS. The α-glucosidase inhibitory activities of all the novel compounds were evaluated in vitro. The solubility and inhibitory activity of α-glucosidase assays showed that the bis-disaccharide glycosides of triterpene acids possessed higher water solubility and α-glucosidase inhibitory activities than the bis-monosaccharide glycosides. Among these compounds, maslinic acid

  通过单糖和二糖将山梨酸（MA）和椰油酸（CA）糖基化合成了一系列化合物，并通过标准的光谱方法阐明了衍生物的结构，包括（1）H NMR，（13）C NMR和人力资源管理系统。在体外评估了所有新化合物对α-葡萄糖苷酶的抑制活性。α-葡糖苷酶测定法的溶解度和抑制活性表明，三萜酸的双-二糖苷比双-单糖苷具有更高的水溶性和α-葡糖苷酶抑制活性。在这些化合物中，山梨酸双-乳糖苷（8e，IC50 = 684 µM）和椰油酸双-乳糖苷（9e，IC50 = 428 µM）具有最佳的水溶性，并且9e的抑制活性比阿卡波糖更好（IC50 = 478） µM）。然而，大多数糖基化衍生物具有比母体化合物低的抑制活性，尽管它们的水溶性明显增强。此外，动力学抑制研究表明9e是一种非竞争性抑制剂，并且还讨论了衍生物的构效关系。
• [EN] SYNTHESIS OF TIMOSAPONIN BII<br/>[FR] SYNTHÈSE DE TIMOSAPONINE BII
  申请人：PHYTOPHARM PLC

  公开号：WO2009133401A1

  公开（公告）日：2009-11-05

  The invention provides a synthetic route from sarsasapogenin to timosaponin BII a related compounds. A diketone intermediate is provided, which can advantageously used for in situ assembly of complex sugar moieties of the desired glycone end product. The diketone compound is then selectively reduced using a borohydride reducing agent form the desired end product. Certain of the end products and intermediates are novel compounds per se.

  该发明提供了一种从山楂皂素合成至地黄皂苷BII及相关化合物的合成途径。提供了一种二酮中间体，可以优势地用于在原位组装所需糖苷末端产物的复杂糖基。然后使用硼氢化还原剂选择性还原二酮化合物形成所需的最终产物。其中一些最终产物和中间体本身是新颖的化合物。
• Facile Synthesis of Oleanolic Acid Monoglycosides and Diglycosides
  作者：Yu Sha、Mao-Cai Yan、Jiao Liu、Yang Liu、Mao-Sheng Cheng

  DOI：10.3390/molecules13071472

  日期：——

  condensation of the carboxylic acid with bromo-glycosides was found to be more efficient in the synthesis of 28-glycosides. Two approaches were investigated and proved practicable in the preparation of 3,28- diglycosides. This method is suitable for preparing oleanolic acid glycosides with structural diversity for extensive biological evaluation and structure-activity relationship study, and it also apply new

  齐墩果酸及其苷类是重要的天然产物，具有多种有吸引力的生物活性，如抗肿瘤、抗病毒和抗炎特性。在目前的工作中，15 种带有各种糖基的齐墩果酸皂苷，包括 3-单糖苷、28-单糖苷和 3,28-二糖苷，很容易以高产率合成。选择苄基作为 COOH(28) 基团的保护基团，而不是常用的甲基和烯丙基，以避免最终脱保护的困难。发现碱促进羧酸与溴糖苷的缩合在 28-糖苷的合成中更有效。研究了两种方法并证明在制备 3,28-二糖苷中是可行的。