O-(tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-O-(tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-tetra-O-acetyl-α-D-glucopyranose | 71301-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-O-(tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-tetra-O-acetyl-α-D-glucopyranose
• 英文别名: tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-tetra-O-acetyl-α-D-glucopyranose；peracetyl-α-laminaritriose；Glc2Ac3Ac4Ac6Ac(b1-3)Glc2Ac4Ac6Ac(b1-3)a-Glc1Ac2Ac4Ac6Ac；[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-6-[(2R,3R,4S,5R,6R)-2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxy-4-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 71301-30-9
• 化学式: C₄₀H₅₄O₂₇
• 分子量: 966.853
• InChiKey: GDMGYHOCMHCPHK-JNSNQJLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  335
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  O-(tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-O-(tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-tetra-O-acetyl-α-D-glucopyranose 在 氢溴酸 、 溶剂黄146 作用下， 反应 0.25h， 以76%的产率得到2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  衍生自β-（1,3）-d-葡聚糖的O-和C-糖苷的合成

  摘要：

  合成了一系列β-（1,3）-d-葡聚糖，这些结构特别在低聚物的还原端结合了结构变异。衍生自二糖和三糖的O-和C-糖苷均以良好的总收率和完全的选择性获得。O-糖苷是通过经典的Koenigs-Knorr糖基化获得的，而相应的C-糖苷是通过异头碳的烯丙基化和进一步的交叉复分解反应而获得的。最后，针对两种糖苷酶和两种内切葡聚糖酶评估了该化合物，未观察到抑制活性。

  DOI：

  10.1016/j.carres.2013.07.007
• 作为产物：
  描述：

  methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 在 4 A molecular sieve 、 氰化汞 、 mercury dibromide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 O-(tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-O-(tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-tetra-O-acetyl-α-D-glucopyranose
  参考文献：
  名称：

  The Synthesis of Active-Site Directed Inhibitors of Some β-Glucan Hydrolases

  摘要：

  制备出了 D-葡萄糖、纤维生物糖和片状生物糖的 2,3-环氧丙基、3,4-环氧丁基和 4,5-环氧戊基 β-糖苷。此外，还合成了纤维三糖、片状三糖和另外两种三糖的 4,5-环氧戊基 β-糖苷。此外，还制备了 3,4-环氧丁基 β-纤维二糖苷，并在纤维二糖残基中添加了 14C 标记。

  DOI：

  10.1071/ch9900665

文献信息

• Synthesis of Some Glycosylated Derivatives of 2-Deoxy-2-fluoro-β-laminaribiosyl Fluoride: Another Success for Glycosynthases
  作者：Adrian Scaffidi、Robert V. Stick、Keith A. Stubbs

  DOI：10.1071/ch06394

  日期：——

  The synthesis of 4,6-di-O-acetyl-2-deoxy-2-fluoro-3-O-(tetra-O-acetyl-β-d-glucopyranosyl)-β-d-glucosyl fluoride is described. Upon deacetylation and treatment with α-d-glucopyranosyl fluoride in the presence of a glycosynthase, three products, all 2-deoxy-2-fluoro-β-glycosyl fluorides, could be isolated: a trisaccharide, a tetrasaccharide, and a pentasaccharide. An attempt to convert a trisaccharide glycal into a related difluoride, employing Selectfluor, is also reported.

  本研究描述了 4,6-二-O-乙酰基-2-脱氧-2-氟-3-O-(四-O-乙酰基-β-d-吡喃葡萄糖基)-β-d-吡喃葡萄糖基氟化物的合成。在糖合成酶的作用下，脱乙酰基并用α-d-吡喃葡萄糖基氟化物处理后，可分离出三种产物，均为 2-脱氧-2-氟-β-葡萄糖基氟化物：三糖、四糖和五糖。报告还介绍了利用 Selectfluor 将三糖糖醛转化为相关二氟化物的尝试。
• Freeing anomeric hydroxyl groups of peracetylated oligosaccharides by Aspergillus niger lipase
  作者：Assunta Giordano、Antonio Trincone

  DOI：10.1016/s0040-4039(02)00948-6

  日期：2002.7

  Various peracetylated oligosaccharides (di- to hepta-) are subjected to regioselective hydrolysis by Aspergillus niger lipase hydrolyzing 1-O-acetyl group. Molecular weight, anomeric and interglycosidic linkage configurations play a significant role in the hydrolysis reaction. Useful 1-O-deprotected material can be easily prepared for further chemical elaboration. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Oligo-β-(1 → 3)-glucans: Impact of Thio-Bridges on Immunostimulating Activities and the Development of Cancer Stem Cells
  作者：Balla Sylla、Laurent Legentil、Sujata Saraswat-Ohri、Aruna Vashishta、Richard Daniellou、Hsei-Wei Wang、Vaclav Vetvicka、Vincent Ferrières

  DOI：10.1021/jm500506b

  日期：2014.10.23

  Recent developments of innovative anticancer therapies are based on compounds likely to stimulate the immune defense of the patients. beta-(1 -> 3)-Glucans are natural polysaccharides well-known for their immunostimulating properties. We report here on the synthesis of small oligo-beta-(1 ? 3)-glucans characterized by thioglycosidic linkages. The presence of sulfur atom(s) was not only crucial to prolong in vivo immunoactive activities in time, compared to native polysaccharides, but sulfur atoms also had a direct impact on the development of colorectal cancer stem cells. As a result, a short, pure, and structurally well-defined trisaccharidic thioglucan demonstrated similar activities compared to those of natural laminarin.
• Rational Design of Glycomimetic Compounds Targeting the <i>Saccharomyces cerevisiae</i> Transglycosylase Gas2
  作者：Ignacio Delso、Jessika Valero‐González、Eduardo Marca、Tomás Tejero、Ramón Hurtado‐Guerrero、Pedro Merino

  DOI：10.1111/cbdd.12650

  日期：2016.2

  The transglycosylase Saccharomyces cerevisiae Gas2 (ScGas2) belongs to a large family of enzymes that are key players in yeast cell wall remodeling. Despite its biologic importance, no studies on the synthesis of substrate‐based compounds as potential inhibitors have been reported. We have synthesized a series of docking‐guided glycomimetics that were evaluated by fluorescence spectroscopy and saturation‐transfer difference (STD) NMR experiments, revealing that a minimum of three glucose units linked via a β‐(1,3) linkage are required for achieving molecular recognition at the binding donor site. The binding mode of our compounds is further supported by STD‐NMR experiments using the active site‐mutants Y107Q and Y244Q. Our results are important for both understanding of ScGas2–substrate interactions and setting up the basis for future design of glycomimetics as new antifungal agents.
• RODRIGUEZ, EVELYN B.;STICK, ROBERT V., AUSTRAL. J. CHEM., 43,(1990) N, C. 665-679
  作者：RODRIGUEZ, EVELYN B.、STICK, ROBERT V.

  DOI：——

  日期：——