rhamnosyl thioglycoside | 1185741-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rhamnosyl thioglycoside
• 英文别名: 2-methyl-5-tert-butylphenyl 2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside；[(2S,3R,4R,5R,6S)-5-acetyloxy-6-(5-tert-butyl-2-methylphenyl)sulfanyl-4-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 1185741-89-2
• 化学式: C₂₁H₃₀O₆S
• 分子量: 410.532
• InChiKey: DIAGHUKFDFPCBJ-KXBSQMQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rhamnosyl thioglycoside 、 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  齐墩果酸三糖皂苷的合成和细胞毒性。

  摘要：

  已经以线性或一锅法合成了一系列基于β-接骨蛋白的齐墩果酸型皂苷。细胞活力分析表明，合成的皂苷在三种癌细胞系中均具有抗增殖活性，IC50值为2.4-15.1μM，而二十碳五碳苷A1最有效。结果表明末端单糖的类型和连接位置对这些皂苷对所测试的癌细胞系的细胞毒性和选择性具有明显的影响。这项研究对更有效的抗癌药物的未来发展很有帮助。

  DOI：

  10.1016/j.carres.2017.02.010
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以1.31 g的产率得到rhamnosyl thioglycoside
  参考文献：
  名称：

  Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis

  摘要：

  The first synthesis of two natural triterpenoid saponins, which were isolated from the roots of Pulsatilla chinensis and exhibited excellent in vitro cytotoxic activity against HL-60 cells, was concisely achieved in a convergent approach. We employed an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and trichloroacetimidate donors in one-pot reaction as a key step. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.05.011

文献信息

• A sequential one-pot strategy for the synthesis of triterpenoid saponins in ionic liquid [emim][OTf]
  作者：Yiming Song、Tiantian Guo、Qingchao Liu、Weiguo Song、Fahui Li

  DOI：10.1177/1747519819831866

  日期：2019.1

  1-Ethyl-3-methylimidazolium trifluoromethanesulfonate ([emim][OTf]) is an efficient co-solvent and co-promoter for one-pot sequential glycosylation with the combined use of thioglycosides and trichloroacetimidates (or N-phenyltrifluoroacetimidates) donors at room temperature. One-pot glycosylation is efficient for the synthesis of triterpenoid saponins with the combined use of N-phenyltrifluoroacetimidate donors and 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside donors in [emim][OTf].

  1-乙基-3-甲基咪唑三氟甲磺酸盐([emim][OTf])是一种高效的共溶剂和共催化剂，可与硫代糖苷和三氯乙酰亚胺酯(或N-苯基三氟乙酰亚胺酯)供体在室温下进行一锅式顺序糖基化反应。一锅式糖基化反应对于合成三萜皂苷是高效的，可通过在[emim][OTf]中同时使用N-苯基三氟乙酰亚胺酯供体和2-甲基-5-叔丁基苯基(Mbp)硫代糖苷供体来实现。
• Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives
  作者：Qingchao Liu、Hongchun Liu、Lei Zhang、Tiantian Guo、Peng Wang、Meiyu Geng、Yingxia Li

  DOI：10.1016/j.ejmech.2013.04.016

  日期：2013.6

  Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of alpha-L-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C-3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, alpha-L-rhamnosyl moiety linked to C-2-OH of the first monosaccharide (alpha-L-alabinose, beta-D-xylose, beta-n-galactose or beta-D-glucose) in C-3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.