2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate | 138688-24-1

• 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->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 138688-24-1
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: VQXGIRIBXXZASZ-JHOJVHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-[[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(R)-cyano(phenyl)methoxy]oxan-2-yl]methoxy]oxan-3-yl] benzoate 、 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 以68%的产率得到
  参考文献：
  名称：

  苦杏仁苷异麦芽糖衍生物的便捷合成

  摘要：

  由d-苦杏仁苷分五个步骤合成异麦芽糖三氯乙酰亚胺酸酯7。该系列反应的关键步骤是糖基间键的酸催化重排，从而获得热力学上更稳定的α-端基异构体。该反应也适用于苦杏仁苷的不同的二糖，三糖和四糖衍生物，得到相应的重排产物。

  DOI：

  10.1016/j.tetlet.2004.04.057
• 作为产物：
  描述：

  amygdalin heptabenzoate 在 palladium on activated charcoal ammonium formate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis and Hemolytic Activity of Some Hederagenin Diglycosides

  摘要：

  使用六种商业化双糖（D-细胞二糖、D-乳糖、D-麦芽糖、D-梅里糖、D-金雀异二糖、D-异麦芽糖）的三氯乙酰胺衍生物对苦木苷进行糖苷化反应，得到了高产率的保护皂苷。去保护后得到的皂苷进一步转化为相应的甲基酯。这些合成的苦木苷双糖的溶血活性被测量，以根据附加糖的类型和序列建立游离羧酸和甲基酯皂苷的结构–活性关系。

  DOI：

  10.1248/cpb.52.965

文献信息

• Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α-Glucosidase and α-Amylase Inhibitors
  作者：Tiantian Guo、Shaoping Wu、Sen Guo、Lu Bai、Qingchao Liu、Naisheng Bai

  DOI：10.1002/ardp.201500179

  日期：2015.9

  Sixteen naturally occurring oleanolic acid saponins and their derivatives were synthesized in an efficient and practical strategy, and their inhibitory activities against α‐glucosidase and α‐amylase were evaluated in vitro. Among all the compounds, 28‐O‐monoglucoside 8 exhibited remarkably potent inhibitory activity against α‐glucosidase with an IC50 value of 87.3 µM, which was fivefold stronger than

  以一种有效且实用的策略合成了 16 种天然存在的齐墩果酸皂苷及其衍生物，并在体外评估了它们对 α-葡萄糖苷酶和 α-淀粉酶的抑制活性。在所有化合物中，28-O-单糖苷 8 对 α-葡萄糖苷酶表现出显着的抑制活性，IC50 值为 87.3 µM，是抗糖尿病阿卡波糖的 5 倍。根据初步的构效关系，对于 28-O-单糖苷，末端 α-l-吡喃鼠李糖残基的存在增强了 α-葡萄糖苷酶和 α-淀粉酶的抑制活性。此外，对于 3,28-O-bidesmosides，
• Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase
  作者：Tiantian Guo、Qingchao Liu、Peng Wang、Lei Zhang、Wei Zhang、Yingxia Li

  DOI：10.1016/j.carres.2009.04.024

  日期：2009.7

  The first synthesis of scabiosaponins E (1), F (2), and G (3), three new oleanolic acid saponins with strong inhibitory activity on pancreatic lipase isolated from the Chinese traditional medicinal herb Scabiosa tschiliensis, was efficiently achieved in an one-pot strategy under the combined use of glycosyl trichloro-acetimidates and p-toluene 1-thioglycosides (STol) as donors. (C) 2009 Published by Elsevier Ltd.
• Synthesis and Hemolytic Activity of Some Hederagenin Diglycosides
  作者：Martin Chwalek、Karen Plé、Laurence Voutquenne-Nazabadioko

  DOI：10.1248/cpb.52.965

  日期：——

  Glycosylation of hederagenin with the trichloroacetimidate derivatives of six commercial disaccharides (D-cellobiose, D-lactose, D-maltose, D-melibiose, D-gentiobiose, D-isomaltose) was performed giving the protected saponins in high yields. Deprotection then gave the saponins which were transformed into the corresponding methyl esters. The hemolytic activity of these synthetic hederagenin diglycosides was measured in order to establish structure–activity relationships based on the type and sequence of the attached sugar for the free carboxylic acid and methyl ester saponins.

  使用六种商业化双糖（D-细胞二糖、D-乳糖、D-麦芽糖、D-梅里糖、D-金雀异二糖、D-异麦芽糖）的三氯乙酰胺衍生物对苦木苷进行糖苷化反应，得到了高产率的保护皂苷。去保护后得到的皂苷进一步转化为相应的甲基酯。这些合成的苦木苷双糖的溶血活性被测量，以根据附加糖的类型和序列建立游离羧酸和甲基酯皂苷的结构–活性关系。
• Convenient syntheses of isomaltose derivatives from amygdalin
  作者：Martin Chwalek、Karen Plé

  DOI：10.1016/j.tetlet.2004.04.057

  日期：2004.6

  reactions was the acid catalyzed rearrangement of the inter-glycosydic bond to give the thermodynamically more stable α-anomer. The reaction was also applied to different di-, tri-, and tetrasaccharide derivatives of amygdalin giving the corresponding rearrangement products.

  由d-苦杏仁苷分五个步骤合成异麦芽糖三氯乙酰亚胺酸酯7。该系列反应的关键步骤是糖基间键的酸催化重排，从而获得热力学上更稳定的α-端基异构体。该反应也适用于苦杏仁苷的不同的二糖，三糖和四糖衍生物，得到相应的重排产物。