1,5-anhydro-4,6-O-benzylidene-D-glucitol | 65391-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1,5-anhydro-4,6-O-benzylidene-D-glucitol
• 英文别名: (2R,4aR,7S,8R,8aS)-2-phenylhexahydropyrano-[3,2-d][1,3]dioxine-7,8-diol；(2R,4aR,7S,8R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 65391-44-8
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: KRNWQNYQBBRLMC-ZOLYEBIHSA-N

物化性质

• 熔点：
  163-165 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  456.8±45.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4,6-O-benzylidene-D-glucitol 在 palladium on activated charcoal 吡啶 、 盐酸 、 甲醇 、 sodium hydroxide 、 sodium azide 、 氨 、 氢气 、 sodium 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， -78.0~85.0 ℃ 、41.37 kPa 条件下， 反应 99.25h， 生成 (1R,4R,7S,8R)-2-氧杂-5-氮杂双环[2.2.2]辛烷-7,8-二醇
  参考文献：
  名称：

  Synthesis and evaluation of a bicyclic deo×ymannojirimycin derivative as a potential glycosidase inhibitor

  摘要：

  A bicyclo[2.2.2] analogue of the glycosidase inhibitor 1-deoxynojirimycin, 2,6-anhydro-l-deoxymannojirimycin (6), has been synthesized in nine steps from I,5-anhydro-D-glucitol. This conformationally restricted aza-sugar has been shown to inhibit, albeit weakly, several glycosidase enzymes.

  DOI：

  10.1139/cjc-76-4-431
• 作为产物：
  描述：

  1-deoxy-D-glucose tetraacetate 在 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 生成 1,5-anhydro-4,6-O-benzylidene-D-glucitol
  参考文献：
  名称：

  Out-of-ring Claisen rearrangements are highly stereoselective in pyranoses: routes to gem-dialkylated sugars

  摘要：

  DOI：

  10.1021/jo00187a010

文献信息

• Synthesis of new carbohydrate-derived ketones as organocatalysts in the enantioselective epoxidation of arylalkenes. Part 2: Chiral ketones from sugars
  作者：José M. Vega-Pérez、Margarita Vega-Holm、Ignacio Periñán、Carlos Palo-Nieto、Fernando Iglesias-Guerra

  DOI：10.1016/j.tet.2010.11.033

  日期：2011.1

  A range of new, somewhat complex, stereochemically varied, and structurally related carbohydrate-derived ketones were synthesised by a simple method from the carbohydrate precursor (d-gluco and d-galacto derivatives). The common skeleton possesses the keto function sited on a seven-membered ring fused to positions 2 and 3 of the sugar moiety. Their chirality transfer capability in the dioxirane-mediated

  （新的，有些复杂，立体化学变化，并且结构上相关的碳水化合物衍生的酮甲范围是由从糖类前体的简单方法合成d -葡糖和d -半乳糖衍生物）。共同的骨架具有位于与糖部分的位置2和3融合的七元环上的酮基功能。评估了它们在二环氧乙烷介导的芳基烯烃环氧化反应中的手性转移能力。
• Synthesis and Comparative Structure–Activity Study of Carbohydrate-Based Phenolic Compounds as α-Glucosidase Inhibitors and Antioxidants
  作者：Shota Machida、Saki Mukai、Rina Kono、Megumi Funato、Hiroaki Saito、Taketo Uchiyama

  DOI：10.3390/molecules24234340

  日期：——

  Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure–activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro-d-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.

  合成了二十一种含有碳水化合物基团的天然和非天然酚类化合物，并评估了它们在α-葡萄糖苷酶抑制和抗氧化活性方面的结构-活性关系（SAR）。在1,5-脱氧-D-葡萄糖醇（1,5-AG）核心上改变没食子酸单元的位置导致了α-葡萄糖苷酶抑制活性的变化，特别是当没食子酸单元位于C-2位置时表现出明显的强活性。此外，增加没食子酸单元的数量显著影响了α-葡萄糖苷酶抑制作用，2,3,4,6-四没食子酸-1,5-AG（54）和2,3,4,6-四没食子酸-D-葡萄糖吡喃糖（61）表现出卓越的活性，其α-葡萄糖苷酶抑制活性比没食子酸（37）高出13倍以上。此外，一项比较结构-活性研究表明，碳水化合物核心中的半缩醛羟基官能团和4,6-O-六羟基二苯甲酰（HHDP）单元的双芳基键，包括tellimagrandin I在内的椰子酸鞣质并不是α-葡萄糖苷酶抑制活性所必需的。最后，抗氧化活性随没食子酸单元数量的增加而成比例增加。
• TETRAHYDROPYRAN NUCLEIC ACID ANALOGS
  申请人：Swayze Eric E.

  公开号：US20090092981A1

  公开（公告）日：2009-04-09

  The present disclosure describes tetrahydropyran nucleoside analogs, oligomeric compounds prepared therefrom and methods of using the oligomeric compounds. More particularly, tetrahydropyran nucleoside analogs are provided, having one or more chiral substituents, that are useful for enhancing properties of oligomeric compounds including nuclease resistance and binding affinity. In some embodiments, the oligomeric compounds provided herein hybridize to a portion of a target RNA resulting in loss of normal function of the target RNA.

  本公开描述了四氢吡喃核苷类似物，以及由此制备的寡聚合物化合物和使用这些寡聚合物化合物的方法。更具体地说，提供了具有一个或多个手性取代基的四氢吡喃核苷类似物，这些类似物可用于增强包括核酸酶抗性和结合亲和性在内的寡聚合物化合物的性质。在某些实施例中，本文提供的寡聚合物可以与目标RNA的部分杂交，导致目标RNA失去正常功能。
• Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators
  作者：Guijun Wang、Hao Yang、Sherwin Cheuk、Sherman Coleman

  DOI：10.3762/bjoc.7.31

  日期：——

  Low molecular weight gelators are an important class of molecules. The supramolecular gels formed by carbohydrate derived low molecular weight gelators are interesting soft materials that show great potential for many applications. Previously, we have synthesized a series of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside derivatives and found that several of them are good gelators for water, aqueous

  低分子量凝胶剂是一类重要的分子。由碳水化合物衍生的低分子量凝胶剂形成的超分子凝胶是有趣的软材料，在许多应用中显示出巨大的潜力。以前，我们合成了一系列甲基 4,6-O-亚苄基-α-D-吡喃葡萄糖苷衍生物，并发现其中几种是水、DMSO 水性混合物或乙醇水性混合物的良好胶凝剂。这些糖脂衍生物的胶凝效率取决于它们酰基链的结构。为了了解糖头基的异头位置对自组装的影响，我们合成了一系列 1-脱氧葡萄糖类似物，并检查了它们在几种溶剂中的凝胶特性。几种长链酯，包括含丁二炔的酯，和芳基酯在乙醇、含水乙醇或含水 DMSO 中表现出凝胶化。报道了这些新型类似物的合成和表征。
• Synthesis of a Ring-Oxygenated Variant of the 2-Carboxy-6-hydroxyoctahydroindole Core of Aeruginosin 298-A from Glucose
  作者：Xiaoping Nie、Guijun Wang

  DOI：10.1021/jo0507901

  日期：2005.10.1

  The design and synthesis of a new core structure, a ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole (Choi) from d-glucose, is reported. Choi, a rigid bicyclic unnatural amino acid, is the core structure of about 15 aeruginosins natural compounds. These compounds are thrombin, trypsin, and factor VIIa inhibitors and Choi is important for their biological activity. The ring-oxygenated variant

  报道了新的核心结构的设计和合成，该新的核心结构是来自d-葡萄糖的2-羧基-6-羟基八氢吲哚（Choi）的环加氧变体。Choi是一种刚性的双环非天然氨基酸，是约15种铜绿素酶天然化合物的核心结构。这些化合物是凝血酶，胰蛋白酶和VIIa因子抑制剂，Choi对它们的生物学活性很重要。2-羧基-6-羟基八氢吲哚的环氧化变体可以潜在地用作Choi的替代品，用于基于铜绿素酶的凝血酶抑制剂的设计和合成。