2-O-Acetyl-3,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate | 384371-43-1

• 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: 2-O-Acetyl-3,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2-O-acetyl-3,4,6-tri-O-benzoyl-1-O-(2,2,2-trichloroethanimidoyl)-α-D-glucopyranose；Bz(-3)[Bz(-4)][Bz(-6)]Glc2Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-5-acetyloxy-3,4-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 384371-43-1
• 化学式: C₃₁H₂₆Cl₃NO₁₀
• 分子量: 678.907
• InChiKey: IMYOEWKGDPJXJQ-VYZOEPQYSA-N

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：

  2-O-Acetyl-3,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 Cholest-5-en-3β-yl 3,4,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Du; Zhang; Kong, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 18, p. 2289 - 2293

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 在 吡啶 、 水 作用下， 反应 3.25h， 生成 2-O-Acetyl-3,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Du; Zhang; Kong, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 18, p. 2289 - 2293

  摘要：

  DOI：

文献信息

• Concise Synthesis and Antidiabetic Effect of Three Natural Triterpenoid Saponins Isolated from<i>Fadogia ancylantha</i>(Makoni tea)
  作者：Zi-Li Feng、Shao-Ping Wu、Wen-Hong Li、Tian-Tian Guo、Qing-Chao Liu

  DOI：10.1002/hlca.201500061

  日期：2015.9

  The first concise synthesis of the bidesmosidic oleanolic acid saponins 1–3 isolated from Fadogia ancylantha (Makoni tea) have been accomplished through a ‘one‐pot sequential glycosylation’ strategy with two glycosyl 1‐(trichloroacetimidate)s as glycosyl donors. The synthesized natural products 1–3 were then evaluated for their inhibitory activities against α‐glucosidase, α‐amylase, and lipase. Among

  所述bidesmosidic齐墩果酸皂甙的第一简明合成1 - 3从分离Fadogia ancylantha “ -锅顺序的糖基化一个”具有两个糖基1-（三氯乙酰亚胺酯）S作为糖供体的策略（马科尼茶）已通过来完成的。将合成的天然产物1 - 3然后评价它们对抑制活性α-葡糖苷酶，α-淀粉酶，和脂肪酶。间的测定化合物1 - 3，化合物1表现出较强的α-葡萄糖苷酶和α-淀粉酶抑制，IC 50的160和180μ值中号分别。更以上，化合物2和3显示出对强抑制α葡糖苷酶和脂肪酶，与respectivement IC 50个的170和190μ值中号，以及190和200μ中号。
• Discovery of the First Series of Small Molecule H5N1 Entry Inhibitors
  作者：Gaopeng Song、Sen Yang、Wei Zhang、Yingli Cao、Peng Wang、Ning Ding、Zaihong Zhang、Ying Guo、Yingxia Li

  DOI：10.1021/jm900275m

  日期：2009.12.10

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Inhibition of H5N1 entry into cells may be an effective strategy. We report the first three small molecule inhibitors saponins with 3-O-beta-chacotriosyl residue, which Showed potent inhibitory activity with IC50 of 7.22-9.25 mu M. The subsequent SAR studies showed the 3-O-beta-chacotriosyl residue was essential for the activity, and the aglycone structure also affected the activity.
• Total Synthesis of Quercetin 3-Sophorotrioside
  作者：Yuguo Du、Guohua Wei、Robert J. Linhardt

  DOI：10.1021/jo035722y

  日期：2004.3.1

  5,7-Dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxy- phenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativurn shoots and showing protective effects on liver injury induced by chemicals, was synthesized for the first time. The target compound was successfully synthesized in eight linear steps and in 39% overall yield through a combination of phasetransfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.