phenyl 3,4-di-O-acetyl-2-deoxy-1-thio-L-rhamnopyranoside | 862731-40-6

• 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: phenyl 3,4-di-O-acetyl-2-deoxy-1-thio-L-rhamnopyranoside
• 英文别名: phenyl 3,4-di-O-acetyl-2,6-deoxy-1-thio-L-arabino-hexopyranoside；[(2S,3S,4S)-3-acetyloxy-2-methyl-6-phenylsulfanyloxan-4-yl] acetate
• CAS: 862731-40-6
• 化学式: C₁₆H₂₀O₅S
• 分子量: 324.398
• InChiKey: FRRHXGZIXGLODC-QCHGBURNSA-N

物化性质

• 沸点：
  425.6±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-di-O-acetyl-2-deoxy-1-thio-L-rhamnopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.17h， 生成 phenyl 3-O-benzoyl-2-deoxy-1-thio-β-L-rhamnopyranoside
  参考文献：
  名称：

  糖肽糖基转移酶合成效用的系统研究

  摘要：

  参与细菌次级代谢产物生物合成的糖基转移酶可用于生成生物活性天然产物的糖修饰类似物。一些糖基转移酶具有宽松的底物特异性，并且已经假定滥交是该类的一个特征。作为探索这些酶合成效用计划的一部分，我们使用纯化的酶和化学合成的 TDP β- 分析了将类似的 2-脱氧-L-糖连接到万古霉素型糖肽苷元的糖基转移酶的底物选择性。 2-脱氧-L-糖类似物。我们表明，虽然这些糖肽糖基转移酶中的一些是混杂的，但其他糖肽糖基转移酶只能容忍它们将处理的底物的微小修改。例如，糖基转移酶 GtfC 和 GtfD，分别将 4-epi-L-vancosamine 和 L-vancosamine 转移到万古霉素假糖苷和氯定向素 B 的葡萄糖单元的 C-2，显示出适度放松的供体底物特异性对其天然苷元的糖基化。相比之下，GtfA，一种将 4-epi-L-vancosamine 连接到苄基位置的转移酶，仅利用与其天然 TDP 糖底

  DOI：

  10.1021/ja052945s
• 作为产物：
  描述：

  2-deoxy-3,4-di-O-acetyl-L-rhamnopyranose 在 咪唑 、 氯化锆(IV) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 3,4-di-O-acetyl-2-deoxy-1-thio-L-rhamnopyranoside
  参考文献：
  名称：

  2-脱氧-1-O-甲硅烷基化-β-己吡喃糖。有用的糖基供体和合成中间体。

  摘要：

  以高立体选择性和高收率合成了不同的2-脱氧-1-O-甲硅烷基化-β-己吡喃糖。已经证明了它们在糖苷和糖基供体的直接合成以及在端基异构中心的其他合成上有用的转化中的应用。

  DOI：

  10.1016/s0040-4039(00)71241-x

文献信息

• Re-Exploring the Anthracycline Chemical Space for Better Anti-Cancer Compounds
  作者：Merle A. van Gelder、Sabina Y. van der Zanden、Merijn B. L. Vriends、Roos A. Wagensveld、Gijsbert A. van der Marel、Jeroen D. C. Codée、Herman S. Overkleeft、Dennis P. A. Wander、Jacques J. C. Neefjes

  DOI：10.1021/acs.jmedchem.3c00853

  日期：2023.8.24

  capacity to induce DNA- and chromatin damage. This coherent set of data allowed us to deduce a few guidelines on anthracycline design, as well as discover novel, highly potent anthracyclines that may be better tolerated by patients.

  蒽环类抗癌药物在临床上广泛用于治疗多种癌症。它们会产生 DNA 双链断裂，但最近引入染色质损伤的诱导作为抗癌活性的另一个主要决定因素。这两个事件的结合导致了所报告的副作用。虽然我们对蒽环类药物的结构-活性关系的了解有所提高，但许多结构变异仍然没有得到很好的探索。因此，我们在此报告了一组不同的蒽环类药物的制备方法，这些蒽环类药物在糖部分、胺烷基化模式、糖链和糖苷配基方面存在差异。我们评估了相关人类癌细胞系的体外细胞毒性，以及诱导 DNA 和染色质损伤的能力。这组连贯的数据使我们能够推断出一些关于蒽环类药物设计的指南，并发现患者可能更好耐受的新型高效蒽环类药物。
• Syntheses and Biological Activities of 3‘-Azido Disaccharide Analogues of Daunorubicin against Drug-Resistant Leukemia
  作者：Guisheng Zhang、Lanyan Fang、Lizhi Zhu、Yanqiang Zhong、Peng George Wang、Duxin Sun

  DOI：10.1021/jm050916m

  日期：2006.3.1

  Anthracyclines, such as daunorubicin (DNR) and doxorubicin (Dox), are widely used for cancer therapy but are limited by drug resistance and cardiotoxicity. To overcome drug resistance, we synthesized a novel class of disaccharide analogues of DNR against drug-resistant leukemia. In these disaccharide analogues (1-6) the first (inner) sugar in the carbohydrate chain is a 3-azido-2,3,6-trideoxy-L-lyxo-alpha-hexopyranose; the second (outer) sugars that are linked via alpha(1 -> 4) to the first sugar are a series of uncommon sugars. Their cytotoxicities were examined in drug-sensitive leukemia cells K562 and doxorubicin-resistant K562/Dox cells by MTS assay. In drug-sensitive cells, compounds 1-6 were found to be active against leukemia K562 cells with IC50 in the nanomolar range (200-1100 nM), while compounds 2-5 with 2,6-dideoxy sugars showed better activity than compounds 1 and 6 with 2,3,6-trideoxy sugars. In doxorubicin-resistant K562/Dox cells, compounds 1, 3, and 5 exhibited much better activities (with IC50 between 0.29 and 2.0 mu M) than DNR (with IC50 > 5 mu M). Compound 3 emerged as the most active compound, showing at least 17-fold higher activity against drug-resistant cells than parent compound DNR. The IC50 values of compound 3 in both drug-sensitive and drug-resistant cells are identical, which indicates that compound 3 completely overcomes drug resistance. Structure-activity relationship (SAR) studies showed that the substitution and orientation of the 3-OH group in the second sugar significantly influence its activity against drug-resistant leukemia. These results suggest that sugar modifications of anthracyclines change their activity and overcome drug resistance.
• WO2006/124720
  申请人：——

  公开号：——

  公开（公告）日：——
• Tagged Hypervalent Iodine Reagents:  A New Purification Concept Based on Ion Exchange through S_N2 Substitution
  作者：Eike Kunst、Florian Gallier、Gilles Dujardin、Mekhman S. Yusubov、Andreas Kirschning

  DOI：10.1021/ol702319p

  日期：2007.12.1

  The preparation of phenylsulfonate-tagged iodine(III) reagents as well as their use in a novel purification strategy for iodine(III)-promoted reactions is described. The concept is based on ion exchange and is initiated by an azide-promoted S(N)2-reaction at the alkyl sulfonate followed by trapping of the resulting aryl sulfonate anion with an ion-exchange resin. The concept is successfully proven for Ru-catalyzed oxidations of alcohols, the activation and glycosidation of thioglycosides, and the Suarez reaction of pyranoses.