3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)propanol | 167990-44-5

• 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)propanol
• 英文别名: 3-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)propanol；3-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]propan-1-ol
• CAS: 167990-44-5
• 化学式: C₃₀H₃₆O₅
• 分子量: 476.613
• InChiKey: GNEJISYXVBFZAL-DKIMQPOESA-N

物化性质

• 沸点：
  599.8±50.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)propanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到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：

  3-(α-L-fucopyranosyl)-prop-1-ene 在 sodium hydride 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.0h， 生成 3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)propanol
  参考文献：
  名称：

  [EN] GLUCOSE-RESPONSIVE INSULIN CONJUGATES
  [FR] CONJUGUÉS D'INSULINE SENSIBLES AU GLUCOSE

  摘要：

  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）。

  公开号：

  WO2016164288A1

文献信息

• 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）。
• Sweet and Salted: Sugars Meet Hydroxyapatite
  作者：Laura Cipolla、Francesco Nicotra、Monica Sandri、Antonino Natalello、Davide Bini、Luca Gabrielli

  DOI：10.1055/s-0030-1260953

  日期：2011.8

  Carbonated hydroxyapatite (CHA) has been successfully biodecorated with carbohydrate derivatives, via silylation of the hydroxy groups of the apatite and subsequent covalent bonding with a suitably functionalized carbohydrate moiety. The presented procedure opens the way toward covalent biofunctionalisation of CHA with carbohydrates.

  通过对磷灰石的羟基进行硅烷化处理，然后与适当功能化的碳水化合物分子进行共价键合，碳化羟基磷灰石（CHA）成功地与碳水化合物衍生物进行了生物装饰。该方法开辟了碳水化合物共价生物功能化 CHA 的道路。
• Glucose-responsive insulin conjugates
  申请人：Merck Sharp & Dohme Corp.

  公开号：US09427475B2

  公开（公告）日：2016-08-30

  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.

  本发明公开了胰岛素共轭物，包括一个胰岛素分子与至少一个双叉联接物共价结合，该联接物具有两个臂，每个臂独立地连接到一个配体，该配体包括一个糖和至少一个联接物的糖苷，其中至少一个联接物的糖苷为岩藻糖。即使在没有外源多价糖结合分子（如Con A）的情况下，这些胰岛素共轭物显示出对系统浓度的糖类（如葡萄糖或α-甲基甘露糖）的药代动力学（PK）和/或药效学（PD）特性的响应，即当其被用于需要该物质的患者时。
• US9427475B2
  申请人：——

  公开号：US9427475B2

  公开（公告）日：2016-08-30
• US9884125B2
  申请人：——

  公开号：US9884125B2

  公开（公告）日：2018-02-06