6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate | 331969-97-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Glc6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-2-(acetyloxymethyl)-4,5-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 331969-97-2
• 化学式: C₃₁H₂₆Cl₃NO₁₀
• 分子量: 678.907
• InChiKey: LMPRSGVCSGTWDZ-VYZOEPQYSA-N

物化性质

• 熔点：
  81-83 °C
• 沸点：
  701.3±70.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 在 TMSOTf 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 dodecyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside
  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
• 作为产物：
  描述：

  1,6-anhydro-2,3,4-tri-O-benzoyl-β-D-glucopyranose 在 硫酸 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 47.0h， 生成 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
  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

• A general strategy for the synthesis of 3,6-branched gluco-oligosaccharides: facile synthesis of the phytoalexin elicitor oligosaccharides
  作者：Jun Ning、Yuetao Yi、Fanzuo Kong

  DOI：10.1016/s0040-4039(02)01143-7

  日期：2002.8

  A general method for the synthesis of 3,6-branched gluco-oligosaccharides has been developed. As a typical example of the method, the synthesis of the glucohexatose phytoalexin elicitor on a large scale was achieved via coupling of a trisaccharide donor with a trisaccharide acceptor. The donor and acceptor were prepared easily from 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose, 2,3,4,6-tetra-O-ben

  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。
• Synthesis of Pentasaccharide and Heptasaccharide Derivatives and Their Effects on Plant Growth
  作者：Hongmei Liu、Shuihong Cheng、Jun Liu、Yuguang Du、Zhihui Bai、Yuguo Du

  DOI：10.1021/jf800326r

  日期：2008.7.1

  Two oligosaccharide derivatives, beta-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-beta-D-Glcp-(1-4)-alpha-D-ManpOMe (1) and beta-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-beta-D-Glcp-(1-4)-alpha-D-ManpOMe (2), have been synthesized efficiently using a convergent glycosylation strategy of 2 + 3 and 2 + 5. 1,6-Anhyclro-beta-D-glucopyranose, which was prepared from cotton pyrolysis, was applied as a key synthon in the synthesis, significantly simplifying the preparation. The bioassay suggested that these two oligosaccharides can both stimulate the growth of maize cultured in liquid medium at a concentration of 3 ppm.
• 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.