phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α/β-L-lyxo-hexopyranoside | 755033-91-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α/β-L-lyxo-hexopyranoside
• 英文别名: [(2S,3S,4S)-4-azido-2-methyl-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 755033-91-1
• 化学式: C₁₄H₁₇N₃O₃S
• 分子量: 307.373
• InChiKey: NMLSBVHAEGMGJS-ROGFAUGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α/β-L-lyxo-hexopyranoside 在 sodium hydroxide 、 六氟磷酸银 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 7-(3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)daunorubicinone
  参考文献：
  名称：

  A divergent approach to 3-azido-2,3,6-trideoxy-l-hexoses from rhamnal

  摘要：

  An alternative strategy has been developed for producing 3-azido-2,3,6-trideoxy-L-hexoses, protected forms of daunosamine, ristosamine, acosamine, and epi-daunosamine. This method involved BF3-OEt2-induced peroxidation of rhamnal to construct key intermediate alpha,beta-unsaturated lactone as the common precursor. After further derivatization, four 3-azido hexoses were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.062
• 作为产物：
  描述：

  (4S,5S,6S)-4-Azido-6-methyl-tetrahydro-pyran-2,5-diol 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α/β-L-lyxo-hexopyranoside
  参考文献：
  名称：

  A divergent approach to 3-azido-2,3,6-trideoxy-l-hexoses from rhamnal

  摘要：

  An alternative strategy has been developed for producing 3-azido-2,3,6-trideoxy-L-hexoses, protected forms of daunosamine, ristosamine, acosamine, and epi-daunosamine. This method involved BF3-OEt2-induced peroxidation of rhamnal to construct key intermediate alpha,beta-unsaturated lactone as the common precursor. After further derivatization, four 3-azido hexoses were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.062

文献信息

• Glycosylation of glycopeptides: a comparison of chemoenzymatic and chemical methods
  作者：Catherine Leimkuhler、Zhong Chen、Ryan G. Kruger、Markus Oberthür、Wei Lu、Christopher T. Walsh、Daniel Kahne

  DOI：10.1016/j.tetasy.2004.12.006

  日期：2005.1

  hard to explore carbohydrate diversity in biologically active glycosylated natural products and their derivatives. In this paper we compare the efficiency of chemical and enzymatic methods for glycosylation of glycopeptides related to vancomycin and describe the parameters that should be considered in designing synthetic approaches to glycosylated natural product derivatives.

  糖基化复杂分子仍然是主要的合成挑战，这使得难以探索具有生物活性的糖基化天然产物及其衍生物中的碳水化合物多样性。在本文中，我们比较了与万古霉素有关的糖肽的糖基化的化学和酶促方法的效率，并描述了设计糖基化天然产物衍生物的合成方法时应考虑的参数。
• 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.
• A Practical Method for the Stereoselective Generation of β-2-Deoxy Glycosyl Phosphates
  作者：Markus Oberthür、Catherine Leimkuhler、Daniel Kahne

  DOI：10.1021/ol049187f

  日期：2004.8.1

  beta-2-Deoxy sugar nucleotides are substrates used by a variety of glycosyltransferases (Gtfs). We have developed a chemical route to synthesize beta-2-deoxy sugar phosphates that starts from a-glycosyl chlorides. Our approach reliably provides access to a range of NDP beta-2-deoxy sugars essential for studying glycosyltransferases involved in the synthesis of biologically active natural products.