2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucopyranose | 331969-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucopyranose
• 英文别名: 2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)]-1,2-O-isopropylidene-α-D-glucofuranose；[(2R,3R,4S,5R,6S)-6-[[(3aR,5R,6S,6aR)-5-[(1R)-1-hydroxy-2-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 331969-99-4
• 化学式: C₇₀H₆₄O₂₃
• 分子量: 1273.26
• InChiKey: JQBPKBQYHPSVSF-JUYJYKNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  93
• 可旋转键数：
  29
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  289
• 氢给体数：
  2
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucopyranose 、 生成 Glc(b1-3)[Glc(b1-6)]Glc(b1-6)Glc(b1-6)[Glc(b1-3)]Glc(b1-6)Glc(b1-6)[Glc(b1-3)]Glc
  参考文献：
  名称：

  合成3,6-支链葡萄糖寡糖的一般策略：合成植物抗毒素激动剂寡糖

  摘要：

  已经开发了合成3，6-支链葡萄糖寡糖的通用方法。作为该方法的典型实例，通过三糖供体与三糖受体的偶联来大规模合成葡萄糖己糖植物抗毒素。供体和受体可以容易地由1,2：5,6-二-O-异亚丙基-α-d-呋喃呋喃糖，2,3,4,6-四-O-苯甲酰基-α-d-吡喃葡萄糖基三氯乙酰亚胺酸酯和以区域和立体选择性的方式，6 - O-乙酰基-2,3,4-三-O-苯甲酰基-α-d-吡喃葡萄糖基三氯乙酰亚胺酸酯。通过该策略也已经容易地合成了引发剂的高级寡糖，包括七，九，九，十二和十四糖。

  DOI：

  10.1016/s0040-4039(02)01143-7
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 三氟甲磺酸三甲基硅酯 、 氨 、 potassium carbonate 、 溶剂黄146 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 82.0h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucopyranose
  参考文献：
  名称：

  Phytoalexin-Elicitor Active β-(1→3)-Branched β-(1→6)-连接七葡萄糖及其十二烷基糖苷的高效合成

  摘要：

  采用 1,2:5,6-二-O-异亚丙基-α-D-呋喃葡萄糖、2,3,4,6-四O-苯甲酰基-α-D-吡喃葡萄糖基三氯乙酰亚胺酯和6-O-乙酰基-2,3,4-三-O-苯甲酰基-α-D-吡喃葡萄糖基三氯乙酰亚胺酯通过区域选择性和立体选择性方式进行。使用开发的策略制备了具有植物抗毒素诱导剂活性的β-(1→3)-支链β-(1→6)-连接的七葡萄糖1及其十二烷基糖苷2。生物测定表明，十二烷基 β-(1→3)-支链 β-(1→6)-连接的六葡萄糖苷 2 的植物抗毒素诱导剂活性略高于相应的还原端游离七葡萄糖 1。

  DOI：

  10.1055/s-2003-37644

文献信息

• Efficient Synthesis of an Allose-Containing Analogue of the Phytoalexin-Elicitor Glucohexaose and Its Dodecyl Glycoside
  作者：Xiangdong Mei、Jun Ning、Hongju Ma、Dewen Qiu、Qianfei Zhao、Yonghong Li

  DOI：10.1055/s-0028-1083292

  日期：2009.1

  analogue 2 of the phytoalexin elicitor β-(1→3)-branched β-(1→6)-linked glucohexatose and its dodecyl glycoside 3 has been regio- and stereospecifically synthesized. As a typical example of the method, the synthesis of 2 was achieved via coupling of the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-β-d-glucopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-d-glucopyranosyl-(1→6)]-1,2-O-isopropylidene-α-d-allopyranosyl

  已经在区域和立体上特异性地合成了植物抗毒素素引发剂β-（1→3）-分支的β-（1→6）-连接的葡萄糖己糖的含Allose的类似物2和其十二烷基糖苷3。作为该方法的典型实例，通过三糖供体2,3,4,6-四-O-苯甲酰基-β - d-吡喃葡萄糖基- （1→3）-[2,3]的偶联来完成2的合成。具有三糖受体的，4，6-四-O-苯甲酰基-β - d-吡喃吡喃糖基-（（1→6）]-1,2 - O-异亚丙基-α - d-戊吡喃糖基三氯乙酰亚胺酸酯（9）。供体很容易从1,2：5,6-二-O-异亚丙基-α-制备d-铝呋喃糖（5）和2,3,4,6-四-O-苯甲酰基-α - d-吡喃葡萄糖基三氯乙酰亚胺酸酯（4）以区域和立体选择性的方式。 寡糖-合成-糖苷-糖基化-立体选择性
• Large-Scale Preparation of the Phytoalexin Elicitor Glucohexatose and Its Application as a Green Pesticide
  作者：Jun Ning、Fanzuo Kong、Bangmao Lin、Huide Lei

  DOI：10.1021/jf020683x

  日期：2003.2.1

  Large-scale preparation of the phytoalexin elicitor was achieved through a highly regio- and sterereoselective synthesis using 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (1), 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (2), and 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (3) as the synthons. Coupling of 1 with 2 gave the 1-->3-linked disaccharide; subsequent selective removal of 5,6-O-isopropylidene to give 5 followed by selective 6-O-glycosylation with 1 afforded the trisaccharide 6. Hydrolysis to remove the 1,2-O-isopropylidene was accompanied by ring expansion, giving 3,6-branched pyranosyl trisaccharide. Acetylation, selective 1-O-deacetylation, and activation with trichloroacetonitrile gave the trisaccharide donor 7. The trisaccharide acceptor 9 was prepared from condensation of the disaccharide 5 with 3 and subsequent 6-O-deacetylation. Coupling of the trisaccharide donor 7 with the trisaccharide acceptor 9 and subsequent deprotection afforded the glucohexatose elicitor. The cost of the produced glucohexatose should be low enough to allow its applications in agriculture as a green pesticide. At a concentration of 5-10 mg/L, the resultant elicitor was used to treat growing orange trees and harvested oranges, giving very encouraging results, comparable with those obtained using commercial pesticides at a concentration of 1400 mg/L (Topsin-M) for growing trees and 900 mg/L (Tecto) for harvested oranges, respectively. Treatment of tomato leaves against Botrytis cinerea with the synthetic elicitor at a concentration of 10 mg/L gave 82% inhibition, comparable with the inhibition of 84% by Wanmeiling at a concentration of 1000 mg/L. Treatment of tea leaves also showed promising results.