2-deoxy-2-fluoro-3,5-di-O-benzoyl-D-arabinofuranosyl bromide | 98855-71-1

• 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: 2-deoxy-2-fluoro-3,5-di-O-benzoyl-D-arabinofuranosyl bromide
• 英文别名: ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate；[(2R,3R,4S)-3-benzoyloxy-5-bromo-4-fluorooxolan-2-yl]methyl benzoate
• CAS: 98855-71-1
• 化学式: C₁₉H₁₆BrFO₅
• 分子量: 423.235
• InChiKey: YYVZPZJEMLBIGM-LVYZTWJOSA-N

物化性质

• 沸点：
  492.3±45.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-fluoro-3,5-di-O-benzoyl-D-arabinofuranosyl bromide 在 ammonium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 非阿尿苷
  参考文献：
  名称：

  Vaidyanathan, G.; Affleck, D. J.; Welsh, P., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 91 - 93

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 在 四丁基氟化铵 、 氢溴酸 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以94%的产率得到2-deoxy-2-fluoro-3,5-di-O-benzoyl-D-arabinofuranosyl bromide
  参考文献：
  名称：

  一种绿色合成氯法拉滨医药中间体的方法

  摘要：

  本发明涉及一种绿色合成氯法拉滨医药中间体的方法，具体包括如下步骤：将式II化合物溶于有机溶剂中，冰浴下加入40％的氢溴酸、四丁基氟化铵，搅拌反应3小时后，加入三乙胺三氢氟酸盐，继续搅拌反应2‑3小时，即得式I化合物。

  公开号：

  CN109320567A

文献信息

• Nucleoside process
  申请人：Bristol-Myers Company

  公开号：US04625020A1

  公开（公告）日：1986-11-25

  Process for producing 1-halo-2-deoxy-2-fluoroarabinofuranoside derivatives bearing protective ester groups from 1,3,5-tri-O-acylribofuranose; the 1-halo compounds are intermediates in the synthesis of therapeutically active nucleosidic compounds.

  从1,3,5-三-O-酰基核糖呋喃糖中制备带有保护酯基团的1-卤代-2-脱氧-2-氟阿拉伯呋喃苷衍生物的生产过程；这些1-卤化合物是合成具有治疗活性的核苷类化合物的中间体。
• Compounds and oligomeric compounds comprising novel nucleobases
  申请人：——

  公开号：US20040033973A1

  公开（公告）日：2004-02-19

  The present invention relates to nucleoside compositions comprising novel nucleobases and oligomeric compounds comprising at least one such nucleoside. These oligomeric compounds typically have enhanced binding affinity properties compared to oligomeric compounds without the modification. The oligomeric compounds are useful, for example, for investigative and therapeutic purposes.

  本发明涉及包含新型核碱基的核苷酸组合物以及包含至少一种此类核苷酸的寡聚合物化合物。这些寡聚合物化合物通常具有比没有这种修饰的寡聚合物化合物更强的结合亲和性能。这些寡聚合物化合物可用于调查和治疗等用途。
• Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides
  作者：Petr Nauš、Pavla Perlíková、Radek Pohl、Michal Hocek

  DOI：10.1135/cccc2011082

  日期：——

  A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleosides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding (protected) 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium eventually followed by deprotection. Key intermediate 6-chloro-7-deazapurine 2′-C-methyl-β-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl-protected 1,2-anhydro-2-C-methylribofuranose. The 1,2-anhydro sugar was synthesized in 3 steps starting from readily available 2-C-methylribonolactone. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3′,5′-protected 6-chloro-7-deazapurine ribofuranoside via 2′-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.

  一系列新型糖基修饰的细胞毒性6-杂环-7-脱氮嘌呤核苷衍生物：2'-C-甲基核糖核苷、阿拉伯核苷和带有烷基、芳基和杂芳基团的位置6的2'-脱氧-2'-氟阿拉伯核苷，通过钯催化的相应（受保护的）6-氯（7-氟）-7-脱氮嘌呤核苷与（杂）芳基硼、杂芳基锡烷和三甲基铝的交叉偶联反应制备，最终通过去保护反应得到。关键中间体6-氯-7-脱氮嘌呤2'-C-甲基-β-D-核糖呋喃苷通过具有立体选择性的核碱基负离子糖基化与对甲苯基保护的1,2-脱氧-2'-C-甲基核糖呋喃糖制备而成。1,2-脱氧糖在3步合成，起始原料为易得的2-C-甲基核糖内酯。6-氯-7-脱氮嘌呤阿拉伯呋喃苷中间体通过从3′,5′-保护的6-氯-7-脱氮嘌呤核糖苷经2'-羟基氧化再还原而获得。所有制备的化合物均未显示出明显的细胞毒性或抗病毒活性。
• Synthesis and anti-HIV activity of 2′-fluorine modified nucleoside phosphonates: Analogs of GS-9148
  作者：Richard L. Mackman、Kuei-Ying Lin、Constantine G. Boojamra、Hon Hui、Janet Douglas、Deborah Grant、Oleg Petrakovsky、Vidya Prasad、Adrian S. Ray、Tomas Cihlar

  DOI：10.1016/j.bmcl.2007.11.126

  日期：2008.2

  Modified purine analogs of GS-9148 [5-(6-amino-purin-9-yl)-4-fluoro-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (2'-Fd4AP) were synthesized and their anti-HIV potency evaluated. The antiviral activity of guanosine analog (2'-Fd4GP) was comparable that of to 2'-Fd4AP in MT-2 cells, but selectivity was reduced.

  合成了GS-9148 [5-（6-氨基-嘌呤-9-基）-4-氟-2,5-二氢呋喃-2-基氧基甲基]-膦酸（2'-Fd4AP）的修饰嘌呤类似物，他们的抗艾滋病毒效力进行了评估。鸟嘌呤类似物（2'-Fd4GP）的抗病毒活性与MT-2细胞中2'-Fd4AP的抗病毒活性相当，但选择性降低。
• SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
  申请人：FUJIFILM Corporation

  公开号：US20150152131A1

  公开（公告）日：2015-06-04

  A compound represented by a formula [1D] as shown below (wherein R 1A , R 1B , R 2A , R 2B , R 3A and R 3B represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, and the like) is useful as an intermediate for producing a thionucleoside, and the production method of the present invention is useful as a method for producing a thionucleoside.

  下列的化合物，其化学式为[1D]（其中R1A、R1B、R2A、R2B、R3A和R3B代表氢原子、可选择取代的C1-6烷基等），可作为生产硫代核苷的中间体，本发明的生产方法可作为一种生产硫代核苷的方法。