allyl 3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside | 666727-75-9

• 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: allyl 3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS: 666727-75-9
• 化学式: C₄₅H₄₄O₁₄
• 分子量: 808.836
• InChiKey: NGMKLCAJEURAEH-JEVMQIQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  59.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  152.74
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  allyl 3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 甲醇 、 potassium carbonate 、 palladium dichloride 作用下， 以 二氯甲烷 为溶剂， 生成 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
  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：

  2-PROPENYL4,6-O-BENZYLIDENE-Α-D-GLUCOPYRANOSIDE2-丙烯基4,6-O-亚苄基-Α-D-吡喃葡萄糖苷 在 吡啶 、 甲醇 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 palladium dichloride 作用下， 以 二氯甲烷 为溶剂， 生成 allyl 3-O-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-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 (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.