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 | 824402-83-7

• 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-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: allyl bis[2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)]-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS: 824402-83-7
• 化学式: C₆₃H₆₀O₁₉
• 分子量: 1121.16
• InChiKey: SMDUEBYFEIZRRE-MZDZAZRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  82.0
• 可旋转键数：
  16.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  209.89
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate 、 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 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到
  参考文献：
  名称：

  Synthesis of (R)-2,3-epoxypropyl(1→3)-β-d-pentaglucoside

  摘要：

  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.

  DOI：

  10.1016/j.carres.2005.01.015
• 作为产物：
  描述：

  allyl 3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 甲醇 、 tetrafluoroboric acid 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 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

文献信息

• Synthesis of Laminarin Fragments and Evaluation of a β-(1,3) Glucan Hexasaccaride-CRM₁₉₇Conjugate as Vaccine Candidate against<i>Candida albicans</i>
  作者：Roberto Adamo、Marta Tontini、Giulia Brogioni、Maria Rosaria Romano、Gabriele Costantini、Elisa Danieli、Daniela Proietti、Francesco Berti、Paolo Costantino

  DOI：10.1080/07328303.2011.604453

  日期：2011.5

  Laminarin-CRM197 glycoconjugates were previously demonstrated to be immunogenic and confer protection against Candida albicans in mice. Laminarin consists of β-(1,3) glucan repeating units, with sporadic β-(1,6) branches. A set of short glucans was used to study the effect of the β-(1,6) branch on the antigenicity of linear β-(1,3) glucans. A linear β-(1,3) glucan hexasaccharide was selected as the

  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。