3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene | 167990-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene
• 英文别名: 1-allyl-1-deoxy-2,3,4-tri-O-benzyl-alpha-L-fucopyranose；(2S,3R,4R,5R,6S)-2-methyl-3,4,5-tris(phenylmethoxy)-6-prop-2-enyloxane
• CAS: 167990-42-3
• 化学式: C₃₀H₃₄O₄
• 分子量: 458.598
• InChiKey: WBMQTRIOEYMRSN-DKIMQPOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 双氧水 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-(tri-O-benzyl-α-L-fucopyranosyl)-1-propyl bromide
  参考文献：
  名称：

  Design and synthesis of C-linked fucosides as inhibitors of E-selectin

  摘要：

  Two series of C-linked fucosides as mimetics for the tetrasaccharide sialyl Lewis X have been synthesized and tested as inhibitors of E-Selectin. The fucopeptides have been prepared from three key intermediates, including alpha-C-allyl fucose, natural and unnatural amino acids bearing hydroxyl groups and an alpha,omega-diacid moiety for the imitation of the essential three parts of SLe(x), i.e., the Fuc, Gal, and NeuAc. The nature and distance of the linkage of the fucose moiety to the amino acids as well as the distance between the amino acids and the terminal carboxylic acid group turned out to be crucial for the biological activity. In addition the necessity of both OH groups (4- and 6-OH) in the Gal part could be confirmed. Conformational NMR study of the most active mimetic supports the structure-activity relationship. A second series of mimetics was prepared, where Fuc and Gal moieties were purely C-linked. In the synthesis of beta-C-allyl galactose an intramolecular 1,2-hydride shift led to an interesting side product. However, the substituted glycosidic oxygens led to a substantial loss of conformational constrain, which could not be compensated and resulted in low activity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00127-7
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-fucopyranose 在 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene
  参考文献：
  名称：

  C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

  摘要：

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02121-1

文献信息

• Design, synthesis and biological evaluation of aryl-substituted sialyl Lewis X mimetics prepared via cross-metathesis of C-fucopeptides
  作者：Christoph M Huwe、Thomas J Woltering、Jan Jiricek、Gabriele Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1016/s0968-0896(98)00245-4

  日期：1999.5

  been developed as sialyl Lewis X mimetics. Although the compounds have a much simpler structure compared to SLe(x), up to 3-times higher binding affinity toward E-selectin and > 1000 times toward P-selectin was observed. Furthermore, a convenient strategy for generating a number of analogues from a SLe(x) mimetic template at a very late stage of the synthesis was introduced, using a ruthenium catalyzed

  已经开发了几种芳基取代的C-岩藻肽作为唾液酸化的路易斯X模拟物。尽管与SLe（x）相比，这些化合物的结构要简单得多，但观察到的对E-选择素的结合亲和力高达3倍，对P-选择素的结合亲和力高达1000倍。此外，介绍了在台式条件下使用钌催化的交叉烯烃复分解反应在合成的非常后期从SLe（x）模拟模板生成许多类似物的便捷策略。
• GLUCOSE-RESPONSIVE INSULIN CONJUGATES
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150105317A1

  公开（公告）日：2015-04-16

  Insulin conjugates comprising an insulin molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule such as Con A.

  本发明涉及胰岛素共轭物，包括将胰岛素分子共价连接至至少一个双齿配体的连接物中，每个配体独立连接到包含一种含糖和其中至少一个连接物的配体的糖类，其中连接物的至少一个配体的糖类为岩藻糖。这些胰岛素共轭物展示出对系统浓度的糖类（如葡萄糖或α-甲基甘露糖）具有响应的药代动力学（PK）和/或药效动力学（PD）特性，即使在给予需要的受试者时，也不需要外源多价糖类结合分子（如Con A）。
• 1,5-Hydrogen Atom Transfer/Surzur–Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems
  作者：Elisa I. León、Ángeles Martín、Adrián S. Montes、Inés Pérez-Martín、María del Sol Rodríguez、Ernesto Suárez

  DOI：10.1021/acs.joc.1c01376

  日期：2021.11.5

  alkoxyl radicals were generated by the reaction of the corresponding N-alkoxyphthalimides with group 14 hydrides [n-Bu3SnH(D) and (TMS)3SiH], and in comparative terms, the reaction was also initiated by visible light photocatalysis using the Hantzsch ester/fac-Ir(ppy)3 procedure. Special attention was devoted to the influence of the relative stereochemistry of the centers involved in the radical sequence

  已经在一系列具有 3 -C- ( α, β- d , l - 吡喃葡萄糖基）1-丙醇和C -（α- d , l -吡喃葡萄糖基）甲醇结构，由手性池d - 和l - 糖制备。使用乙酰氧基和二苯氧基磷酸酯氧基作为离去基团可有效构建 10-deoxy-1,6-dioxaspiro[4.5]decane 和 4-deoxy-6,8-dioxabicyclo[3.2.1]octane 骨架。烷氧基自由基由相应的N反应生成-烷氧基邻苯二甲酰亚胺与第 14 族氢化物 [ n -Bu 3 SnH(D) 和 (TMS) 3 SiH]，比较而言，该反应也由使用 Hantzsch 酯/ fac -Ir(ppy) 3程序的可见光光催化引发. 特别关注自由基序列中涉及的中心的相对立体化学对反应结果的影响。将BF 3 •Et 2 O 作为催化剂添加到自由基序列中导致所需双环缩酮的产率显着增加。
• [EN] GLUCOSE-RESPONSIVE INSULIN CONJUGATES<br/>[FR] CONJUGUÉS D'INSULINE SENSIBLES AU GLUCOSE
  申请人：MERCK SHARP & DOHME

  公开号：WO2016164288A1

  公开（公告）日：2016-10-13

  Insulin conjugates comprising an insulin analog molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule such as Con A.

  包含胰岛素类似物分子的胰岛素共轭物，与至少一个双齿配体连接物共价连接，每个配体独立连接到一个含有糖类的配体，并且连接物中至少一个配体的糖类是富马醇。这些胰岛素共轭物显示出对糖类（如葡萄糖或α-甲基甘露糖）的体内浓度响应的药代动力学（PK）和/或药效动力学（PD）特性，即使在向需要者施用时，也无需外源多价糖类结合分子（如Con A）。
• Selectin binding glycopeptides
  申请人：Glycomed Incorporated

  公开号：US05508387A1

  公开（公告）日：1996-04-16

  Glyco-amino acids or glycopeptides that have three-dimensionally stable configuration for the presentation of functional groups, fucose, or an analogue or derivative thereof, covalently linked to an amino acid or peptide with a free carboxylic acid group, that facilitate binding between those groups and receptors on selectins, represented by the general structural formula I.

  具有三维稳定构型以呈现功能基团的糖基氨基酸或糖基肽，富马酸或其类似物或衍生物与具有自由羧酸基团的氨基酸或肽共价连接，促进这些基团与选择素受体之间的结合，其一般结构式为I。