2,3,4-tri-O-acetyl-α-L-fucopyranose | 40591-54-6

• 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-acetyl-α-L-fucopyranose
• 英文别名: [(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 40591-54-6
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: QHOCNNVTMIFDFP-BSOOIWJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-fucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89.6%的产率得到2,3,4-tri-O-acetyl-L-fucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Preparation and characterization of 6I,6n-di-O-(l-fucopyranosyl)-β-cyclodextrin (n=II–IV) and investigation of their functions

  摘要：

  Three positional isomers of 6(I),6(n)-di-O-(beta-L-fucopyranosyl)-cyclomaltoheptaose [61,6(n)-di-O-(beta-L-Fuc)-beta-cyclodextrin, -beta CD, n = II-IV] were chemically synthesized using the corresponding authentic compounds, 6(I),6(n)-di-O-(tert-butyidimethylsilyl)-beta CD (n = II-IV), as the fucosyl acceptors, and 2,3,4-tri-O-acetyl-L-fucopyranosyl trichloroacetimidate as the fucosyl donor. Their structures were analyzed by HPLC, MS, and NMR spectroscopy. The hemolytic activities of L-Fuc-beta CDs were lower than that of beta CD, while the solubilities of these branched CDs in water were much higher than that of beta CD. The molecular interaction between these compounds and the fucose-binding lectin Aleuria aurantia lectin (AAL) was investigated using an optical biosensor based on a surface plasmon resonance (SPR) technique. The order of binding affinity, as a function of the fucose-binding position, was 6(I),6(IV)- 6(I),6(III)- > 6(I),6(II)-di-O-(beta-L-Fuc)-beta CD > 6-O-(beta-L-Fuc)-beta CD. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.06.016
• 作为产物：
  描述：

  1,2,3,4-四-O-乙酰基-Alpha-L-岩藻吡喃糖苷 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以40%的产率得到2,3,4-tri-O-acetyl-α-L-fucopyranose
  参考文献：
  名称：

  Preparation and characterization of 6I,6n-di-O-(l-fucopyranosyl)-β-cyclodextrin (n=II–IV) and investigation of their functions

  摘要：

  Three positional isomers of 6(I),6(n)-di-O-(beta-L-fucopyranosyl)-cyclomaltoheptaose [61,6(n)-di-O-(beta-L-Fuc)-beta-cyclodextrin, -beta CD, n = II-IV] were chemically synthesized using the corresponding authentic compounds, 6(I),6(n)-di-O-(tert-butyidimethylsilyl)-beta CD (n = II-IV), as the fucosyl acceptors, and 2,3,4-tri-O-acetyl-L-fucopyranosyl trichloroacetimidate as the fucosyl donor. Their structures were analyzed by HPLC, MS, and NMR spectroscopy. The hemolytic activities of L-Fuc-beta CDs were lower than that of beta CD, while the solubilities of these branched CDs in water were much higher than that of beta CD. The molecular interaction between these compounds and the fucose-binding lectin Aleuria aurantia lectin (AAL) was investigated using an optical biosensor based on a surface plasmon resonance (SPR) technique. The order of binding affinity, as a function of the fucose-binding position, was 6(I),6(IV)- 6(I),6(III)- > 6(I),6(II)-di-O-(beta-L-Fuc)-beta CD > 6-O-(beta-L-Fuc)-beta CD. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.06.016

文献信息

• Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group
  作者：Hariprasad Vankayalapati、Gurdial Singh

  DOI：10.1039/b002754p

  日期：——

  The synthesis of the disaccharides α-L-Fucp-(1,2)- and α-L-Fucp-(1,3)-β-D-Galp(1)-4-methylumbelliferone as fucosidase substrates was accomplished by activation of the anomeric centre of 2,3,4-tri-O-acetyl- and 2,3,4,6-tetra-O-acetyl-α,β-L-fuco- and -D-galactopyranosyl propane-1,3-diyl phosphates with TMSOTf and with minimal protection of 4-methylumbelliferyl β-D-galactopyranoside.

  合成双糖α-L-岩藻糖-(1,2)-和α-L-岩藻糖-(1,3)-β-D-半乳糖-(1)-4-甲基伞花素作为岩藻糖苷酶底物，通过用TMSOTf激活2,3,4-三-O-乙酰基和2,3,4,6-四-O-乙酰基α,β-L-岩藻糖和-D-半乳糖基丙烷-1,3-二醇磷酸盐的异头中心，并对4-甲基伞花素β-D-半乳糖苷进行了最小保护。
• 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）。
• [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）。
• Sequential Dy(OTf)₃-Catalyzed Solvent-Free Per-<i>O</i>-Acetylation and Regioselective Anomeric De-<i>O</i>-Acetylation of Carbohydrates
  作者：Yi-Ling Yan、Jiun-Rung Guo、Chien-Fu Liang

  DOI：10.1002/asia.201700867

  日期：2017.9.19

  regioselective anomeric de‐O‐acetylation of carbohydrates can be tuned by adjusting the reaction medium. In this study, the per‐O‐acetylation of unprotected sugars by using a near‐stoichiometric amount of acetic anhydride under solvent‐free conditions resulted in the exclusive formation of acetylated saccharides as anomeric mixtures, whereas anomeric de‐O‐acetylation in methanol resulted in a moderate‐to‐excellent

  镝（III）三氟甲磺酸催化的per- ö -acetylation和区域选择性的端基异构脱ö碳水化合物-acetylation可以通过调节反应介质进行调谐。在这项研究中，在无溶剂条件下，通过使用接近化学计量的乙酸酐对未保护的糖进行过O-乙酰化，导致乙酰化糖类作为异头混合物独家形成，而异头De- O在甲醇中进行乙酰化可产生中等至优异的收率。与各种未保护的单糖或二糖的反应，然后半单步顺序转化为相应的乙酰化糖基半缩醛，也可导致高收率。此外，在Dy（OTf）3催化的糖基化反应后，获得的半缩醛可以成功转化为三氯亚氨酸盐。
• The tertiary-butyl group: Selective protection of the anomeric centre and evaluation of its orthogonal cleavage
  作者：Afraz Subratti、Nigel Kevin Jalsa

  DOI：10.1016/j.tetlet.2018.04.048

  日期：2018.5

  The tertiary-butyl group has not been examined extensively as a protecting group. In this work, we describe the synthesis of tert-butyl glycosides via the Fischer glycosylation protocol. Furthermore, its utility as a temporary anomeric protecting group was evaluated. A range of differentially protected monosaccharides was used to investigate the stability of the tert-butyl group upon the introduction

  在第三丁基组尚未被广泛讨论的一个保护基。在这项工作中，我们描述了通过Fischer糖基化方案合成叔丁基糖苷。此外，评估了其作为临时端基保护基的用途。一系列差异保护的单糖用于研究引入其他保护基团后叔丁基的稳定性。在后者存在下其裂解的相容性。