2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal | 157506-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal
• 英文别名: [(2R,3R,4S,5R)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4-methylsulfonyloxyoxolan-2-yl]methyl methanesulfonate
• CAS: 157506-35-9
• 化学式: C₁₀H₁₈O₁₀S₂
• 分子量: 362.379
• InChiKey: SHPDTJHOCNWEOS-LURQLKTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal 在 吡啶 、 盐酸 、 三氟乙酸 、 calcium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 106.0h， 生成 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allose
  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
• 作为产物：
  描述：

  乙二醇 、 1,2-O-isopropylidene-3,5,6-tri-O-methanesulfonyl-β-L-idofuranose 在 对甲苯磺酸 作用下， 反应 13.0h， 以60%的产率得到2,5-anhydro-3,6-di-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

• Antitumour tiazofurin analogues embedded with an amide moiety at the C-2′ position
  作者：Mirjana Popsavin、Miloš Svirčev、Ljilja Torović、Gordana Bogdanović、Vesna Kojić、Dimitar Jakimov、Saša Spaić、Lidija Aleksić、Velimir Popsavin

  DOI：10.1016/j.tet.2011.06.090

  日期：2011.9

  bromopyruvate, and finally to target C-nucleosides by treatment with ammonia in methanol. In vitro cytotoxicities of tiazofurin analogues against a number of human tumour cell lines were recorded and compared with those observed for the parent molecule (tiazofurin), as well as the commercial antitumour agent doxorubicin (DOX). Analogues 2b–d have shown a potent in vitro cytotoxic activity against human myelogenous

  从d-葡萄糖开始已经完成了四种新的噻唑呋林类似物的合成。合成的关键步骤是三步骤级联反应，该步骤使有效的硫化氢介导的2-叠氮基-3- O-酰基-呋喃呋喃糖基氰化物一锅转化为相应的2-烷基酰胺基呋喃核糖基硫代羧酰胺。通过与溴丙酮酸乙酯的环缩合反应，首先将所得的关键中间体转化为受保护的噻唑啉衍生物，最后通过在甲醇中用氨处理，将其转化为目标C-核苷。记录了噻唑呋喃类似物对多种人类肿瘤细胞系的体外细胞毒性，并将其与亲本分子（噻唑呋林）以及市售抗肿瘤药阿霉素（DOX）观察到的毒性进行了比较。类似物2b – d显示了对人骨髓性白血病K562的有效体外细胞毒活性。在实体瘤细胞系中，HT29仅对2d敏感，而HeLa细胞对2a，2b和2d敏感。只有类似物2a对MCF-7细胞具有高度的细胞毒性。没有噻唑呋林类似物对正常的胎儿肺MRC-5细胞表现出任何明显的细胞毒性。Bcl-2的下调，caspase-3的激活和P
• 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。
• Divergent synthesis of two novel muscarine analogues from D-glucose
  作者：Velimir Popsavin、Mirjana Popsavin、Ljubica Radić、Ostoja Berić、Vera Ćirin-Novta

  DOI：10.1016/s0040-4039(99)01952-8

  日期：1999.12

  A divergent synthesis of two new muscarine analogues bearing the (5S)-dioxolanyl isosteric group was achieved starting from d-glucose, enabling access to libraries of potential muscarinic agonists or antagonists. The key step of the synthesis involved a regioselective epoxide ring opening in 2,5:3,4-dianhydro derivatives 5 and 15 with LiAlH4, whereby the natural stereochemistry of (+)-muscarine (1)

  从d-葡萄糖开始，实现了两个新的带有（5 S）-二氧戊环基等规基团的新毒蕈碱类似物的合成，从而可以访问潜在的毒蕈碱激动剂或拮抗剂库。合成的关键步骤涉及在具有LiAlH 4的2,5：3,4-二脱水衍生物5和15中的区域选择性环氧化物开环，从而使（+）-毒蕈碱（1）和（-）-同素异形-有效地建立了毒蕈碱（2）。
• Synthesis and antiproliferative activity of two new tiazofurin analogues with 2′-amido functionalities
  作者：Mirjana Popsavin、Ljilja Torović、Miloš Svirčev、Vesna Kojić、Gordana Bogdanović、Velimir Popsavin

  DOI：10.1016/j.bmcl.2006.02.001

  日期：2006.5

  Two novel tiazofurin analogues 2 and 3 were synthesized starting from D-glucose. The key step of the synthesis was the efficient one-step hydrogen sulfide-mediated conversion of 2-azido-3-O-acyl-ribofuranosyl cyanides to the corresponding 2-amido thiocarboxamides. Compounds 2 and 3 were evaluated for their in vitro antiproliferative activity against certain human tumour cell lines. Remarkably, compound 2 was found to be 570-fold more potent than tiazofurin against MCF-7 cells, while compound 3 showed the most powerful cytotoxicity against HT-29 cancer cells, being almost 100-fold more active than tiazofurin. (C) 2006 Elsevier Ltd. All rights reserved.
• 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.