3-(1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)prop-1-ene | 53263-18-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)prop-1-ene
• 英文别名: 3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-propene；1-deoxy-1-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-propene；1-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；3-(2,3,4,6-tetra-O-acetyl-b-d-galactopyranosyl)-1-propene；allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-prop-2-enyloxan-2-yl]methyl acetate
• CAS: 53263-18-6；82659-53-8；98920-44-6；98920-46-8；98920-49-1；103773-87-1；98920-48-0
• 化学式: C₁₇H₂₄O₉
• 分子量: 372.372
• InChiKey: LJLBJVZTDBJHTM-BQJWPVKWSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  416.8±38.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)prop-1-ene 在 甲醇 、 Amberlite IR 400 (OH-) resin 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4:6-p-methoxybenzylidene-β-D-galactopyranosyl)-1-propene
  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：

  2,3,4,6-tetra-O-acetyl-1-bromo-β-D-galactopyranosyl chloride 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.83h， 生成 3-(1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)prop-1-ene
  参考文献：
  名称：

  立体控制获取高糖（非 1-en-4-ulopyranosyl 衍生物）和糖模拟物 [3-(β-D-Glycopyranosyl)-1-propenes and (3Z)-4,8-​​Anhydro-nona-1,3-二烯醇]

  摘要：

  全乙酰化 1-溴-β-D-吡喃葡萄糖基氯与烯丙基三丁基锡在光解条件下反应，得到相应的乙酰化 α-D-non-1-en-4-ulopyranosyl 氯。产量不同，主要取决于母糖的配置（D-葡萄糖：86%；D-半乳糖：51%；D-甘露糖：31%）。水解产生的相应乙酰化 α-D-non-1-en-4-ulopyranoses 作为副产物获得（8-23% 产率）。由 nBu3SnH 介导的乙酰化 α-D-non-1-en-4-ulopyranosyl 氯化物的自由基还原导致 glycopyranos-1-yl 自由基，其非对映选择性猝灭产生乙酰化 3-(β-D-glycopyranosyl)- 1-丙烯具有良好的总产率（50-57% 产率）。这种方法结合了涉及吡喃糖基自由基的 C-C 和 C-H 键形成反应，构成了乙酰化 3-(β-D-吡喃葡萄糖基)-1-丙烯的更有效途径。没有检测到 3-(α-

  DOI：

  10.1002/1099-0690(200008)2000:16<2831::aid-ejoc2831>3.0.co;2-0

文献信息

• Synthesis of <i>C</i> ‐Glycosyl Amino Acid Building Blocks Suitable for the Solid‐Phase Synthesis of Multivalent Glycopeptide Mimics
  作者：Niels R. M. Reintjens、Tony S. Koemans、Nick Zilverschoon、Riccardo Castelli、Robert A. Cordfunke、Jan Wouter Drijfhout、Nico J. Meeuwenoord、Herman S. Overkleeft、Dmitri V. Filippov、Gijsbert A. Marel、Jeroen D. C. Codée

  DOI：10.1002/ejoc.202000587

  日期：2020.8.31

  C-glycosyl functionalized lysine building blocks, featuring C-glycosidic derivatives of alpha-rhamnose, alpha-mannose, alpha-galactose, beta-galactose, and beta-N-acetyl glucosamine have been designed and synthesized. These derivatives, equipped with acid-labile protecting groups, are eminently suitable for solid-phase synthesis of multivalent glycopeptides. The lysine building blocks were prepared fromC-allyl

  已经设计并合成了五个 C-糖基功能化赖氨酸构件，其特征是 α-鼠李糖、α-甘露糖、α-半乳糖、β-半乳糖和β-N-乙酰氨基葡萄糖的 C-糖苷衍生物。这些衍生物带有酸不稳定保护基团，非常适合多价糖肽的固相合成。赖氨酸结构单元由 C-烯丙基糖苷制备，该糖苷经历了与丙烯酸酯的 Grubbs 交叉复分解，然后还原所得 α,β-不饱和酯中的 C=C 双键，并释放羧酸酯以允许缩合带有赖氨酸侧链。将由此得到的C-糖苷共五种，用于三种糖肽的固相肽合成(SPPS)，
• Combining Glycomimetic and Multivalent Strategies toward Designing Potent Bacterial Lectin Inhibitors
  作者：Yoann M. Chabre、Denis Giguère、Bertrand Blanchard、Jacques Rodrigue、Sylvain Rocheleau、Mathieu Neault、Subhash Rauthu、Alex Papadopoulos、Alexandre A. Arnold、Anne Imberty、René Roy

  DOI：10.1002/chem.201003402

  日期：2011.5.27

  As part of ongoing activities toward the design of potent and selective ligands against galactoside‐binding proteins from animal, bacterial, and plant lectins, a systematic investigation involving the synthesis and binding evaluations of a series of original β‐C‐galactopyranoside mimetics is described. The multivalent presentation of partly optimized candidates on various dendritic scaffolds through

  作为针对来自动物，细菌和植物凝集素的半乳糖苷结合蛋白的有效和选择性配体设计工作的一部分，对系统的研究进行了描述，该研究涉及一系列原始β- C-吡喃半乳糖苷模拟物的合成和结合评估。通过Cu I催化的叠氮化物-炔烃环加成反应（CuAAc），还实现了在各种树突状支架上部分优化的候选物的多价呈现。基于等温滴定量热法（ITC）的生物物理研究已经表明在低微摩尔范围内的解离常数为最佳优化单价缀合物（ķ d = 37μ中号）。因此，结果证实了稳定的C-半乳糖苷可能代表了致病性铜绿假单胞菌PA-IL凝集素（Lec A）的天然α-连接寡糖抑制剂的有效合成糖模拟物。对于三价，六价和九价衍生物，还观察到糖缀合物亲和力的惊人增强，其中最有力的解离常数低于500 n M，与β- D相比，亲和力增加了400倍。-Gal- Ø‐我用作参考。为了加深我们对识别过程中涉及的最佳糖模拟物结合模式的理解，已进行了分子建模研究，对
• Carbohydrate triazoles and isoxazoles as inhibitors of galectins-1 and -3
  作者：Denis Giguère、Ramesh Patnam、Marc-André Bellefleur、Christian St-Pierre、Sachiko Sato、René Roy

  DOI：10.1039/b517529a

  日期：——

  Galactosides and lactosides bearing triazoles or isoxazoles, regiospecifically prepared by [1,3]-dipolar cycloadditions between alkynes, azides or nitrile oxides, provided specific galectin-1 and -3 inhibitors with potencies as low as 20 µM.

  通过炔类、叠氮化物或腈类氧化物之间的[1,3]-二极环加成反应，对含有三唑或异噁唑的半乳糖苷和乳糖苷进行了区域特异性制备，提供了特异性的 galectin-1 和-3 抑制剂，其效力低至 20 µM。
• Thiol–ene click chemistry for the synthesis of highly effective glycosyl sulfonamide carbonic anhydrase inhibitors
  作者：Mohamed-Chiheb Saada、Joanna Ombouma、Jean-Louis Montero、Claudiu T. Supuran、Jean-Yves Winum

  DOI：10.1039/c3cc42541j

  日期：——

  Thiol-ene click chemistry has been applied for obtaining sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors incorporating sugar moieties. Most of these new compounds were moderate CA I inhibitors, effective CA II inhibitors, and low nanomolar/subnanomolar inhibitors of the tumor-associated isoforms CA IX and XII.

  硫醇-点击化学已用于获得掺入糖部分的磺酰胺碳酸酐酶（CA，EC 4.2.1.1）抑制剂。这些新化合物中的大多数是中度CA I抑制剂，有效的CA II抑制剂以及与肿瘤相关的同工型CA IX和XII的低纳摩尔/亚纳摩尔分子抑制剂。
• 3-Substituted 1-Naphthamidomethyl-C-galactosyls Interact with Two Unique Sub-Sites for High-Affinity and High-Selectivity Inhibition of Galectin-3
  作者：Alexander Dahlqvist、Santanu Mandal、Kristoffer Peterson、Maria Håkansson、Derek T. Logan、Fredrik R. Zetterberg、Hakon Leffler、Ulf J. Nilsson

  DOI：10.3390/molecules24244554

  日期：——

  The galectins are a family of galactose-binding proteins playing key roles in inflammatory processes and cancer. However, they are structurally very closely related, and discovery of highly selective inhibitors is challenging. In this work, we report the design of novel inhibitors binding to a subsite unique to galectin-3, which confers both high selectivity and affinity towards galectin-3. Olefin

  半乳糖凝集素是一个半乳糖结合蛋白家族，在炎症过程和癌症中起关键作用。然而，它们在结构上非常密切相关，高选择性抑制剂的发现具有挑战性。在这项工作中，我们报告了与 galectin-3 特有的亚位点结合的新型抑制剂的设计，该亚位点对 galectin-3 具有高选择性和亲和力。烯丙基 β-C-吡喃半乳糖和 1-乙烯基萘之间的烯烃交叉复分解或氨基甲基 β-C-吡喃半乳糖与 1-萘甲酸衍生物的酰化产生带有 1-萘酰胺结构元素的 C-吡喃半乳糖，该结构元素与亚半乳糖凝集素-3 独特位点相互作用对两种抑制剂-galectin-3 复合物的分子建模和 X 射线结构分析。亲和力降至亚 µM，选择性高于半乳糖凝集素-1、2、4个N端域、4个C端域、7、8个N端域、9个N端域和9个C端域均较高。这些结果表明，通过靶向独特的亚位点可以实现对单一半乳糖凝集素的高亲和力和选择性，这为进一步开发小而选择性的半乳糖凝集素抑制剂提供了希望。