2,2'-anhydro-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)thymine | 145819-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,2'-anhydro-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)thymine
• 英文别名: (2R,4R,5R,6R)-5-bromo-11-methyl-4-(trityloxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one
• CAS: 145819-53-0
• 化学式: C₂₉H₂₅BrN₂O₄
• 分子量: 545.433
• InChiKey: DJDJBMHRYVIKFK-HIQYAUPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-anhydro-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)thymine 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以93%的产率得到1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine
  参考文献：
  名称：

  Minamoto, Katsumaro; Oishi, Masataka; Kakehi, Akikazu, Journal of the Chemical Society. Perkin transactions I, 1994, # 16, p. 2289 - 2296

  摘要：

  DOI：
• 作为产物：
  描述：

  (5S,6S)-2,2'-anhydro-5-bromo-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-6-methoxy-5,6-dihydrothymine 在 碳酸氢钠 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以81%的产率得到2,2'-anhydro-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)thymine
  参考文献：
  名称：

  Minamoto, Katsumaro; Oishi, Masataka; Kakehi, Akikazu, Journal of the Chemical Society. Perkin transactions I, 1994, # 16, p. 2289 - 2296

  摘要：

  DOI：

文献信息

• Synthesis of 2,2′-Anhydro-1-(3′-deoxy-3′-bromo-β-D-arabinofuranosyl)thymine and Its Derivatives from 5′-<i>O</i>-Trityl-2′,3′-thymidinene
  作者：Katsumaro Minamoto、Masataka Oishi、Akikazu Kakehi、Kenji Watanabe、Toyohide Takeuchi

  DOI：10.1246/cl.1992.2149

  日期：1992.11

  Reaction of 5′-O-trityl-2′,3′-thymidinene with hypobromous acid gave 2,2′-anhydro-1-(3′-deoxy-3′-bromo-5′-O-trityl-β-D-arabinofuranosyl)-(5R,6R)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine (3) and its (5S,6S) trans analogue (4). These were transformed into the corresponding 5,6-epoxy analogues. Compounds 3 and 4 were debromohydrinated to the title 2,2′-anhydro nucleoside in high yields.

  5'-O-trityl-2',3'-thymidinene 与次溴酸反应得到 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D -arabinofuranosyl)-(5R,6R)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine (3) 及其 (5S,6S) 反式类似物 (4)。这些被转化为相应的 5,6-环氧类似物。化合物 3 和 4 以高产率脱溴氢化为标题 2,2'-脱水核苷。
• Reactions of Some 2,3-Anhydro Pyrimidine Nucleosides with Dilithium Tetrahalocuprates
  作者：Kenji Watanabe、Kazufumi Yanagihara、Katsumaro Minamoto、Hiroshi Iwasaki

  DOI：10.1080/07328319308016204

  日期：1993.12

  The reaction of 1-(2,3-anhydro-5-O-trityl-beta-D-lyxofuranosyl)-2-O-methyluracil (2a) and its thymine analogue (2b) with dilithium tetrahalocuprates (Li(2)CuX(4)) revealed an excellent to perfect regioselectivity, yielding 2,2'-anhydro-3'-halonucleosides (3a-d), while the same reactions with 2,3-anhdro uracil and thymine nucleosides (5a,b) gave arabinosyl (6a-d) and xylosyl halohydrins (7a-d) with respective product ratios of 7:3 to 8:2 which were estimated after mesylation to 8a-d and 9a-d.
• Minamoto, Katsumaro; Oishi, Masataka; Kakehi, Akikazu, Journal of the Chemical Society. Perkin transactions I, 1994, # 16, p. 2289 - 2296
  作者：Minamoto, Katsumaro、Oishi, Masataka、Kakehi, Akikazu、Ohta, Naoki、Matsuda, Isamu、et al.

  DOI：——

  日期：——