p-tolyl 2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside | 943221-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4R,5R,6S)-5-acetyloxy-4-hydroxy-2-methyl-6-(4-methylphenyl)sulfanyloxan-3-yl] acetate
• CAS: 943221-79-2
• 化学式: C₁₇H₂₂O₆S
• 分子量: 354.424
• InChiKey: DDMDKSVLZJZHNI-CTEYXQFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  p-tolyl 2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-octyloxy-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-4-O-hexanoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  新型杀蚜剂美甲菊苷型低聚鼠李糖苷及其类似物的设计，合成及构效关系。

  摘要：

  低聚糖已被用于农业工业中的环境友好的昆虫防治。为了发现新型的生态友好型农药，设计并合成了具有生物表面活性剂特性的一系列部分乙酰化的低聚羊驼毛2-8号及其类似物9-14，其中一些具有比甚至更强的杀蚜活性。吡me嗪 SAR的初步研究表明，美甲etti类似物的杀蚜活性在很大程度上取决于其结构，包括糖长和糖上的替代物。其中，鼠李糖脂9表现出最强的杀菌活性，LC50为0.019 mmol / L，表明该生物表面活性剂9可能具有用作环境友好型农业农药的潜力。

  DOI：

  10.3390/molecules23010041
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 以2.5 g的产率得到p-tolyl 2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  结构上与美塞替甙6具有细胞毒活性的酰化低聚鼠李糖苷衍生物的合成和生物学评估†

  摘要：

  通过'2 +1 + 1'聚合策略合成了两个与天然产物美塞蒂苷6结构相关的部分酰化的低聚鼠李糖苷衍生物1和2。生物测定结果表明，将乙酰基引入末端L-鼠李糖的2-位有助于改善体外细胞毒性。化合物1在肿瘤细胞系中显示出广泛的体外细胞毒性和潜在的抗多药耐药性。初步的机理研究表明，化合物1可以通过诱导细胞凋亡来抑制细胞生长，从而阻止K562细胞处于S期的细胞周期进程。

  DOI：

  10.1039/c6ob00862c

文献信息

• Total synthesis of cleistetroside-2, partially acetylated dodecanyl tetrarhamnoside derivative isolated from Cleistopholis patens and Cleistopholis glauca
  作者：Zaihong Zhang、Peng Wang、Ning Ding、Gaopeng Song、Yingxia Li

  DOI：10.1016/j.carres.2007.03.014

  日期：2007.7

  The total synthesis of a partially acetylated dodecanyl tetrarhamnoside derivative, cleistetroside-2, which was isolated from Cleistopholis patens and Cleistopholis glauca and showed significant in vitro antibacterial activity against the Gram-positive bacteria, was achieved for the first time.

  首次实现了部分乙酰化的十二烷基四鼠李糖苷衍生物cleistetroside-2的总合成，该衍生物是从Cleistopholis patens和Cleistopholis glauca中分离出来的，并且对革兰氏阳性细菌显示出显着的体外抗菌活性。
• 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。
• Facile Synthesis of Four Natural Triterpene Saponins with Important Antitumor Activity
  作者：Tiantian Guo、Qingchao Liu、Lei Zhang、Peng Wang、Yingxia Li

  DOI：10.1080/00397910903576602

  日期：2011.1.25

  The first synthesis of four natural triterpene saponins, which exhibit significant antitumor activities, was concisely achieved by adopting a stepwise glycosylation. The key intermediate 13 was afforded via Bu2SnO-mediated regioseletive benzoylation. During the preparation of the target compounds, it was found that the α-L-arabinopyranosyl unit in intermediates 17 and 20 existed in the unusual 1 C

  通过采用逐步糖基化，首次合成了四种具有显着抗肿瘤活性的天然三萜皂苷。关键中间体 13 是通过 Bu2SnO 介导的区域选择性苯甲酰化得到的。在目标化合物的制备过程中，发现中间体17和20中的α-L-阿拉伯吡喃糖基单元以异常的1 C 4 构象存在，去除苯甲酰基后，α-L-阿拉伯吡喃糖基单元在典型的 4 C 1 形式。
• Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives
  作者：Ning Ding、Zaihong Zhang、Wei Zhang、Yuexing Chun、Peng Wang、Huimin Qi、Shan Wang、Yingxia Li

  DOI：10.1016/j.carres.2011.07.028

  日期：2011.10

  A series of novel oligorhamnoside derivatives (1-10) and naturally occurring cleistrioside-5 were synthesized and evaluated for their in vitro antibacterial activities. Among them, dirhamnoside derivative 7 and cleistrioside-5 displayed similar antibacterial profiles and exhibited moderate to good inhibitory activities on bacterial growth against a panel of Gram-positive bacteria (MICs <= 4-32 mu g/mL). The results revealed that these two compounds showed selectivity towards bacterial species strictly, without being affected by the antibiotic-resistant/susceptible properties of one species, which suggested that they might have the potential to avoid antibiotic cross-resistance. In addition, the preliminary SARs of this type of oligorhamnoside derivatives on the antibacterial activities were determined. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of cytotoxic activity of novel anthracene l-rhamnopyranosides
  作者：Gaopeng Song、Hongchun Liu、Wei Zhang、Meiyu Geng、Yingxia Li

  DOI：10.1016/j.bmc.2010.05.064

  日期：2010.7

  A series of anthracene L-rhamnopyranosides were designed and synthesized in a practical way and their cytotoxic activity was examined in vitro. Most compounds exhibited both potent cytotoxicity against several tumor cell lines and high DNA binding capacity. The preliminary results showed that subtle modifications of rhamnosyl moiety in anthracene rhamnosides with acetyl group had a selective toxicity for different tumor cells and the displacement of C-10 carbonyl group in emodin by acetylmethylene group was helpful to improve the inhibitory activity. Lipophilicity of the anthracene glycosides was not a crucial factor for cytotoxicity and most molecules with good cytotoxicity could inhibit the catalytic activity of Top2 alpha. (C) 2010 Elsevier Ltd. All rights reserved.