2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal | 157506-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal
• 英文别名: [(2R,3R,4S,5R)-3-benzoyloxy-5-(1,3-dioxolan-2-yl)-4-methylsulfonyloxyoxolan-2-yl]methyl benzoate
• CAS: 157506-37-1
• 化学式: C₂₃H₂₄O₁₀S
• 分子量: 492.504
• InChiKey: QPDDZBAWEKCZGN-YSTOQKLRSA-N

物化性质

• 沸点：
  653.4±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 143.83h， 生成 3,6-anhydro-5,7-di-O-benzoyl-2-deoxy-4-O-methanesulfonyl-D-glucoheptononitrile
  参考文献：
  名称：

  Synthesis and antitumour activity of new tiazofurin analogues bearing a 2,3-anhydro functionality in the furanose ring

  摘要：

  This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-P-Dribofuranosyl)thiazole-4-carboxamide (2',3'anhydro-tiazofurin) and the corresponding alpha- and beta-homo-C-nucleosides, as well as evaluation of their antitumour activities in vitro. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.050
• 作为产物：
  描述：

  2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal
  参考文献：
  名称：

  Preparation of 2,5-anhydro-3,4,6-tri-O-benzoyl-d-allononitrile from d-glucose

  摘要：

  DOI：

  10.1016/0008-6215(94)80029-4

文献信息

• Stereospecific synthesis of two novel cytotoxic pyrazole C-nucleosides from d-glucose
  作者：Mirjana Popsavin、Ljilja Torovic、Saša Spaic、Srdjan Stankov、Velimir Popsavin

  DOI：10.1016/s0040-4039(00)00894-7

  日期：2000.7

  A multistep stereospecific synthesis of two novel pyrazole C-nucleosides 12 and 21 has been achieved starting from d-glucose, by utilizing the 2,5-anhydro-d-glucose ethylene acetal derivative 1 as a divergent intermediate. The C-nucleoside 12 was shown to be a moderate inhibitor of the in vitro growth of N2a and BHK 21 tumor cell lines, whereas 21 showed a moderate cytotoxic activity only against N2a

  通过使用2，5-脱水-d-葡萄糖乙烯乙缩醛衍生物1作为发散中间体，已经从d-葡萄糖开始实现了两个新颖的吡唑C-核苷12和21的多步立体有择合成。所述Ç核苷12被证明是的N2a细胞和BHK 21肿瘤细胞系的体外生长的适度抑制，而21显示出适度的细胞毒性活性仅仅针对N2a细胞。
• Synthesis and biological evaluation of two novel 2′-substituted tiazofurin analogues
  作者：Mirjana Popsavin、Ljilja Torović、Vesna Kojić、Gordana Bogdanović、Velimir Popsavin

  DOI：10.1016/j.tetlet.2004.07.104

  日期：2004.9

  Two novel tiazofurin analogues, 2-(2-benzamido-2-deoxy-β-d-ribofuranosyl)thiazole-4-carboxamide 4 and 2-(2-azido-2-deoxy-β-d-ribofuranosyl)thiazole-4-carboxamide 5, have been synthesized starting from d-glucose and evaluated for their in vitro cytotoxicity against several human leukaemia and solid tumour cell lines.

  两种新型的噻唑啉类似物2-（2-苯甲酰胺基-2-脱氧-β-d-呋喃核糖基）噻唑-4-羧酰胺4和2-（2-叠氮基-2-脱氧-β-d-呋喃核糖基）噻唑-4-羧酰胺5是从d-葡萄糖开始合成的，并评估了其对几种人类白血病和实体瘤细胞系的体外细胞毒性。
• Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties
  作者：Mirjana Popsavin、Ljilja Torović、Saša Spaić、Srdjan Stankov、Agneš Kapor、Zoran Tomić、Velimir Popsavin

  DOI：10.1016/s0040-4020(01)01126-7

  日期：2002.1

  3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2'-benzamido (15) and 3'-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of highly cytotoxic tiazofurin mimics bearing a 2,3-anhydro function in the furanose ring
  作者：Mirjana Popsavin、Saša Spaić、Miloš Svirčev、Vesna Kojić、Gordana Bogdanović、Vjera Pejanović、Velimir Popsavin

  DOI：10.1016/j.tet.2009.06.100

  日期：2009.9

  This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-beta-D-ribofuranosyl)thiazole-4-carboxamide (2',3'-anhydro-tiazofurin) and the corresponding alpha- and beta-homo-C-nucleosides. The synthetic approach was based on a multistep transformation of D-glucose into suitably protected aldonthioamides followed by their subsequent cyclocondensation with ethyl bromopyruvate to form the thiazole ring. Antiproliferative activity of the target molecules is reported against several human tumour cell lines. (C) 2009 Elsevier Ltd. All rights reserved
• Preparation of 2,5-anhydro-3,4,6-tri-O-benzoyl-d-allononitrile from d-glucose
  作者：Mirjana Popsavin、Velimir Popsavin、Nada Vukojević、János Csanádi、Dušan Miljković

  DOI：10.1016/0008-6215(94)80029-4

  日期：1994.7