1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose | 6893-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose
• 英文别名: 3,5-di-O-benzoyl-1,2-O-isopropylidene-α-D-xylofuranose；3,5-di-O-benzoyl-1,2-O-isopropylidene-D-xylofuranose；((3aR,5R,6S,6aR)-6-(Benzoyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate；[(3aR,5R,6S,6aR)-6-benzoyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 6893-67-0
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: ZYVSFZHNWSDHKK-BMQTXXJKSA-N

物化性质

• 沸点：
  505.2±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose 在 咪唑 、 N-碘代丁二酰亚胺 、 硫酸 、 碘 、 溶剂黄146 、 正丁胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 生成 5-氟-1-(2',3'-二脱氧-2',3'-二脱氢β-D-呋喃阿糖基)-胞嘧啶(Dexelvucitabine)
  参考文献：
  名称：

  Synthesis and comparative evaluation of two antiviral agents: β-l-Fd4C and β-d-Fd4C

  摘要：

  The synthesis of beta-D-Fd(4)C was achieved in a stereoselective fashion fi om D-xylose. The antiviral activity and cytotoxicity of beta-D-Fd(4)C was compared with that of beta-L-Fd(4)C and 3TC (Lamivudine). Of the three agents compared, beta-L-Fd(4)C was found to be the most potent antiviral agent. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00599-x
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 68.0h， 生成 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose
  参考文献：
  名称：

  合成并体外抗肿瘤筛选2-（β-d-xylofuranosyl）thiaazole-4-carboxamide和两个新颖的噻唑呋喃类似物，其取代的四氢呋喃二恶唑部分为糖模拟物

  摘要：

  2-（β- d - xylofuranosyl）thiaazole -4-carboxamide（2）和两个新的噻唑呋林类似物与5-羟甲基-2-甲基-四氢呋喃[2,3- d ] [1,3] dioxol-6-已经合成了作为糖模拟物的O1部分（27和28），并评估了它们对一组人类肿瘤细胞系（K562，HL 60，Jurkat，Raji和HeLa）的体外抗肿瘤活性。与以前的文献报道相反，代谢MTT测定显示出对K562（IC 50  = 0.15μM）和HL-60（IC 50  = 0.13μM）细胞的显着细胞毒性为2。流式细胞仪数据表明类似物2的细胞毒性作用与噻唑呋林相反，K562细胞培养物中的K562细胞凋亡可能是由细胞凋亡介导的，而噻唑呋林在24 h后不诱导K562细胞凋亡，因此提示了不同的作用机制。所有三种类似物2，27和28也对Jurkat，Raji和HeLa细胞活性，用IC 50倍在从0

  DOI：

  10.1016/j.bmcl.2012.08.093

文献信息

• A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O
  作者：Qin-Pei Wu、Ming-Xin Zhou、Xiao-Dong Xi、Di Song、Yuan Wang、Hai-Xia Liu、Yun-Zheng Li、Qing-Shan Zhang

  DOI：10.1016/j.tetlet.2008.02.163

  日期：2008.4

  The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)3·xH2O under mild conditions has been developed. Primary hydroxyl-acetonides could be selectively transformed into diacetates in the presence of anomeric acetonides and the anomeric acetonides

  在合成化学中通常需要将丙酮化物转化为相应的二乙酸盐。开发了一种在温和的条件下在Bi（OTf）3 · x H 2 O存在下将丙酮化物直接转化为二乙酸盐的有效方法。可以在异头丙酮化物的存在下将伯羟基丙酮化物选择性地转化为二乙酸盐，并且异头丙酮化物可以可调谐地转化为2-乙酰氧基异丙基或二乙酸盐基团。
• 3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry
  作者：Sofie Meng Andersen、Mads Heuckendorff、Henrik H. Jensen

  DOI：10.1021/acs.orglett.5b00041

  日期：2015.2.20

  Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.
• 2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity
  作者：Mirjana Popsavin、Vesna Kojić、Saša Spaić、Miloš Svirčev、Gordana Bogdanović、Dimitar Jakimov、Lidija Aleksić、Velimir Popsavin

  DOI：10.1016/j.tet.2014.02.035

  日期：2014.4

  Tiazofurin analogues bearing a 5-hydroxymethy1-2-methyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (2 and 3), and two novel thiazole-based acyclo-C-nucleosides 4 and 16 have been synthesized in multistep sequences starting from D-xylose (compounds 2 and 3) or from D-arabinose (compounds 4 and 16). All synthesized analogues showed potent in vitro antitumour activities against a panel of human tumour cell lines. Flow cytometry data suggest that cytotoxic effects of analogues 2-4 and 16 in the culture of 1(562 cells might be mediated by apoptosis. It was also found that these analogues induced changes in cell cycle distribution of 1(562 cells. Results of western blot analysis (upregulation of Bax and downregulation of Bc1-2, activation of caspase-3 and the presence of a PARP cleavage product) suggest that tiazofurin mimics (2-4 and 16) in 1(562 cells induced apoptosis in a caspasedependent way. (C) 2014 Elsevier Ltd. All rights reserved.
• Gosselin, Gilles; Imbach, Jean-Louis, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 597 - 602
  作者：Gosselin, Gilles、Imbach, Jean-Louis

  DOI：——

  日期：——
• A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4–SiO2
  作者：Hai-Xia Liu、Qin-Pei Wu、Yi-Nan Shu、Xi Chen、Xiao-Dong Xi、Ti-Jian Du、Qing-Shan Zhang

  DOI：10.1016/j.carres.2009.08.035

  日期：2009.11

  The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4-SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl beta-D-furanosides with a 2-acetoxyisopropyl group. (C) 2009 Elsevier Ltd. All rights reserved.