per-O-benzoyllactosyl trichloroacetimidate | 473449-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: per-O-benzoyllactosyl trichloroacetimidate
• 英文别名: Trichloroacetimidate 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-α/β-D-galactopyranosyl)-α/β-D-glucopyranoside；2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside trichloroacetimidate；1-O-[2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-D-glucopyranosyl] trichloroacetimidate；4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-D-glucopyranosyl trichloroacetimidate；2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate；[(2R,3R,4S,5R)-4,5-dibenzoyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 473449-32-0
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: HUCNKFYJQPVDLI-NVWBKHJPSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.03
• 重原子数：
  85.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  244.87
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  N-羟乙基丙烯酰胺 、 per-O-benzoyllactosyl trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.03h， 以98%的产率得到2-(acrylamido)ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Investigating Cell Surface Galectin-Mediated Cross-Linking on Glycoengineered Cells

  摘要：

  The galectin family of glycan-binding proteins is thought to mediate many cellular processes by oligomerizing cell surface glycoproteins and glycolipids into higher-order aggregates. This hypothesis reflects the known oligomeric states of the galectins themselves and their binding properties with multivalent ligands in vitro, but direct evidence of their ability to cross-link ligands on a cell surface is lacking. A major challenge in fundamental studies of galectin ligand interactions is that their natural ligands comprise a heterogeneous collection of glyco-conjugates that share related glycan structures but disparate underlying scaffolds. Consequently, there is no obvious means to selectively monitor the behaviors of natural galectin ligands on live cell surfaces. Here we describe an approach for probing the galectin-induced multimerization of glycoconjugates on cultured cells. Using RAFT polymerization, we synthesized well-defined glycopolymers (GPs) functionalized with galectin-binding glycans along the backbone, a lipid group on one end and a fluorophore on the other. After insertion into live cell membranes, the GPs' fluorescence lifetime and diffusion time were measured in the presence and absence of galectin-1. We observed direct evidence for galectin-1-mediated extended cross-linking on the engineered cells, a phenomenon that was dependent on glycan structure. This platform offers a new approach to exploring the "galectin lattice" hypothesis and to defining galectin ligand specificity in a physiologically relevant context.

  DOI：

  10.1021/ja301694s
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose 在 sodium hydride 、 二甲胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 22.0h， 生成 per-O-benzoyllactosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations

  摘要：

  The synthesis of methyl(ethyl) 2-thio-KDO (i.e. 1, 2, 5, 7 and 10) and ethyl 1-thio-LD-Hepp (i.e. 26 and 43) derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/IFOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer L-alpha-D-Hepp-(1 --> 5)-alpha-KDO-2-O-(CH2)3NH2 (37) and tetramer beta-D-Galp-(1 --> 4)-beta-D-Glep-(1 --> 4)-L-alpha-D-Hepp-(1 -->5)-alpha-KDO-2-O-(CH2)3NH2 (47).

  DOI：

  10.1016/s0040-4020(01)88191-6

文献信息

• Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy
  作者：Ying-Hsin Wang、Hsien-Wei Yeh、Hsiao-Wen Wang、Chia-Chun Yu、Jih-Hwa Guh、Der-Zen Liu、Pi-Hui Liang

  DOI：10.1016/j.carres.2013.04.022

  日期：2013.6

  Naturally occurring spirostanol saponins bear a chacotriose, alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyr anose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2' and/or 4' positions of chacotriose is

  天然存在的螺固醇皂苷带有低聚部分的三甘醇，α-L-鼠李糖基-（1-> 2）-[α-L-鼠李糖基-（1-> 4）]-β-D-葡萄糖吡喃糖残基。据信对于生物学活性是重要的。在本文中，描述了一种简明的组合方法的开发，该方法用于合成在chacotriose的2'和/或4'位置上的两个系列的聚糖变体，并研究了叶绿素在3-OH处的糖苷部分的结构-活性关系。发现这些化合物对白血病细胞系CCRF和HL-20的细胞毒性较弱，表明茶三糖部分对于抗癌活性很重要。
• [EN] NOVEL SULFATED OLIGOSACCHARIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'OLIGOSACCHARIDES SULFATÉS
  申请人：PROGEN PHARMACEUTICALS LTD

  公开号：WO2009049370A1

  公开（公告）日：2009-04-23

  The invention relates to novel compounds that have utility as inhibitors of heparan sulfate-binding proteins; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment of a mammalian subject.

  这项发明涉及具有作为肝素硫酸结合蛋白抑制剂的效用的新化合物；包含这些化合物的组合物；以及利用这些化合物和组合物对哺乳动物主体进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗的用途。
• Synthesis of Diverse Seleno‐Glycolipids <i>via</i> the Transacetalization of Selenoacetals
  作者：Hayata Fukuo、Tatsuya Suzuki、Junpei Shimabukuro、Naoko Komura、Hide‐Nori Tanaka、Akihiro Imamura、Hideharu Ishida、Hiromune Ando

  DOI：10.1002/ejoc.202100847

  日期：2021.10.26

  membrane proteins. To expand the scope of available seleno-glycolipids, we established a facile synthesis toward novel mono- and diseleno-glycolipids with various glycan and lipid moieties; this proceeds via transacetalization of selenoacetals and glycosyl imidates. This work demonstrates the first synthesis of diseleno-glycolipids.

  硒糖脂是用于膜蛋白 X 射线结构研究的有吸引力的去污剂。为了扩大可用硒糖脂的范围，我们建立了对具有各种聚糖和脂质部分的新型单和二硒糖脂的简便合成；这通过硒缩醛和糖基亚氨酸酯的转缩醛化进行。这项工作证明了二硒糖脂的首次合成。
• Amphiphilic carbohydrate–phthalocyanine conjugates obtained by glycosylation or by azide–alkyne click reaction
  作者：Mahmut Ali Ermeydan、Fabienne Dumoulin、Tamara V. Basova、Denis Bouchu、Ayşe Gül Gürek、Vefa Ahsen、Dominique Lafont

  DOI：10.1039/b9nj00634f

  日期：——

  Two series of amphiphilic carbohydrate–phthalocyanine conjugates have been prepared either by glycosylation or by copper-catalyzed click coupling. A common precursor, a hydroxylated phthalocyanine, was directly glycosylated or converted into an azido derivative before undergoing grafting of propargyl–carbohydrates by click reaction.

  通过糖基化或铜催化的点击偶联反应，已制备了两系列具有疏水性和亲水性的碳水化合物-酞菁共轭物。一个常见的前体，羟基酞菁，直接进行了糖基化或在点击反应前先转化为叠氮衍生物，然后进行丙炔基-碳水化合物的接枝。
• Synthesis and Antitumor Activity of a New Ergosterol Derivative
  作者：Zhen-Yuan Zhu、Zhen-qian Wang、Fei Liu、Xiao-Cui Liu、Li-Jing Chen、Xiao-Ran Ge、An-Jun Liu、Yong-Min Zhang

  DOI：10.1007/s10600-016-1607-6

  日期：2016.3

  ranosyl-(1→4)-β-D-glucopyranoside) was efficiently synthesized and evaluated for its inhibitory activities against S180 cell lines compared with ergosterol. The structures of all synthesized compounds were fully characterized by spectroscopic data (NMR, MS). The antitumor activity of the new derivative was significantly enhanced compared with ergosterol.

  Ergosterol-3-O-(β-D-吡喃半乳糖基-(1→4)-β-D-吡喃葡萄糖苷)被有效合成并评估其对S180细胞系的抑制活性与麦角固醇相比。所有合成化合物的结构都通过光谱数据（NMR、MS）进行了充分表征。与麦角甾醇相比，新衍生物的抗肿瘤活性显着增强。