allyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside | 824402-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS: 824402-81-5
• 化学式: C₄₃H₄₂O₁₃
• 分子量: 766.799
• InChiKey: QCNPQRVYNBGLEM-GQMWULOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  56.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  146.67
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  allyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 在 tetrafluoroboric acid 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 allyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis, (1→3)-β-d-glucanase-binding ability and phytoalexin-elicitor activity of (R)-2,3-epoxypropyl (1→3)-β-d-pentaglucoside

  摘要：

  The (1-->3)-beta-D-pentaglucoside was synthesized as its (R)-2,3-epoxypropyl glycoside via 2 + 3 strategy. The disaccharide donor 8 was obtained by 3-selective coupling of 2 with 4, followed by deallylation, and trichloroacetimidation. Meanwhile, the trisaccharide acceptor 12 was prepared by coupling of 10 with 4, followed by deacetylation. Condensation of 8 with 12, followed by epoxidation, and deprotection, gave the target pentaoside. The results of these bioassays demonstrated that the (1-->3)-beta-D-glucanase was obviously inactivated by 15 with k(app) = 3.79 x 10(-4) min(-1). At the same time, we found that the 15 was more active as compared to the laminaripentaose in eliciting phytoalexin accumulation in tobacco cotyledon tissue, and it could be kept longer time than laminaripentaose, which indicated it is much more stable than laminaripentaose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.076
• 作为产物：
  描述：

  allyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 在 溶剂黄146 、 乙二胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到allyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  层粘连蛋白片段的合成和β-（1,3）葡聚糖六糖-CRM197偶联物作为抗白色念珠菌疫苗候选物的评价

  摘要：

  先前证明层粘连蛋白-CRM197糖缀合物具有免疫原性，并赋予小鼠抗白色念珠菌的保护作用。层粘连蛋白由β-（1,3）葡聚糖重复单元组成，具有零星的β-（1,6）分支。使用一组短葡聚糖来研究β-（1,6）支链对线性β-（1,3）葡聚糖的抗原性的影响。选择线性β-（1,3）葡聚糖六糖作为能够抑制层粘连蛋白和抗层粘连蛋白抗体结合的最佳片段。然后将六聚体偶联到CRM197上，并在小鼠中诱导显着滴度的特异性抗laminarin抗体，与Lam-CRM197偶联物产生的抗体相当。

  DOI：

  10.1080/07328303.2011.604453

文献信息

• Synthesis of (R)-2,3-epoxypropyl(1→3)-β-d-pentaglucoside
  作者：Gang-Liang Huang、Xin-Ya Mei、Man-Xi Liu

  DOI：10.1016/j.carres.2005.01.015

  日期：2005.3

  The title pentasaccharide was synthesized via a 2 + 3 strategy. The disaccharide donor, 3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl-(1 -> 3)-2-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranosyI trichloroacetimidate (8), was obtained by selective coupling of allyl 2-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranoside with 3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-alpha-D-glueopyranosyl trichloroacetimidate (4), followed by deallylation, and trichloroacetimidation. Meanwhile, the trisaccharide acceptor, allyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl-(1 -> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyrallosyl(1 -> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (12), was prepared by coupling of allyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl-(1 -> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside with 4, followed by deacetylation. Condensation of 8 with 12, followed by epoxidation, and deprotection, gave the target pentaoside. (c) 2005 Elsevier Ltd. All rights reserved.