9-(5-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine | 134665-27-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(5-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine
• 英文别名: 5'-O-acetyl-3'-β-bromo-3'-deoxyadenosine；[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-3-bromo-4-hydroxyoxolan-2-yl]methyl acetate
• CAS: 134665-27-3
• 化学式: C₁₂H₁₄BrN₅O₄
• 分子量: 372.178
• InChiKey: RENPTCJHZPNUOZ-MCOZSMFQSA-N

物化性质

• 沸点：
  637.0±65.0 °C(Predicted)
• 密度：
  2.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(5-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 三氟化硫吗啉 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 2',3'-二脱氧-3'-氟腺苷
  参考文献：
  名称：

  3'-α-氟-2'，3'-二脱氧腺苷的简便合成方法

  摘要：

  摘要利用3'-β-溴在3'-过程中重排至2'-β位置的新方法，开发了一种简便的合成3'-α-氟-2'，3'-二脱氧腺苷（5）的方法。 α氟化。

  DOI：

  10.1081/ncn-120022616
• 作为产物：
  描述：

  9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine 在 一水合肼 作用下， 以 乙醇 为溶剂， 以70%的产率得到9-(5-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  3'-α-氟-2'，3'-二脱氧腺苷的简便合成方法

  摘要：

  摘要利用3'-β-溴在3'-过程中重排至2'-β位置的新方法，开发了一种简便的合成3'-α-氟-2'，3'-二脱氧腺苷（5）的方法。 α氟化。

  DOI：

  10.1081/ncn-120022616

文献信息

• Novel method for the synthesis of 2',3'-unsaturated nucleosides from 2'(3')-acetoxy-3'(2')-halogeno derivatives by using sodium dithionite with viologen as a reductive elimination mediator.
  作者：Yusuke AMINO、Hisao IWAGAMI

  DOI：10.1248/cpb.39.622

  日期：——

  Reductive elimination of vicinal acetylated halohydrins with Na2S2O4 as the reducing agent and viologen as the reduction mediator in a two-phase water-organic system is described. 2', 3'-Unsaturated nucleosides such as 1-(5-O-acetyl-2, 3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine, -hypoxanthine and uracil were obtained from 2'(3')-acetoxy-3'(2')-halogeno derivatives in good yields by meanes of this procedure.

  描述了以 Na2S2O4 为还原剂、紫胶烯为还原介质，在两相水-有机体系中对邻位乙酰化卤素进行还原消除的过程。通过这种方法，从 2'(3')-乙酰氧基-3'(2')-卤代衍生物中获得了 2'、3'-不饱和核苷，如 1-(5-O-乙酰基-2, 3-二脱氧-β-D-甘油-2-戊烯呋喃糖基)腺嘌呤、次黄嘌呤和尿嘧啶，收率很高。
• Synthesis of 2′,3′-Dideoxypurinenucleosides <i>via</i> the Palladium Catalyzed Reduction of 9-(2,5-Di-<i>O</i>-acetyl-3-bromo-3-deoxy-β-<scp>d</scp>-xylofuranosyl)purine Derivatives
  作者：Hiroshi Shiragami、Yusuke Amino、Yutaka Honda、Masayuki Arai、Yasuhiro Tanaka、Hisao Iwagami、Toshihide Yukawa、Kunisuke Izawa

  DOI：10.1080/07328319608002368

  日期：1996.1

  Practical method to produce 2',3'-dideoxypurinenucleosides from 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)purines (1) was developed. High ratio of 2',3 '-dideoxynucleoside to 3'-deoxyribonucleoside was obtained by Selecting the reaction conditions (solvent, pH and/or base), or changing 2'-acyloxy leaving group. The reaction mechanism was studied by deuteration experiments of 1a and 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-beta-D-ribofuranosyl)thymine (12).
• A synthesis of 3′-α-fluoro-2′,3′-dideoxyadenosine via a bromine rearrangement during fluorination with MOST reagent
  作者：Satoshi Katayama、Satoshi Takamatsu、Masaki Naito、Shigehisa Tanji、Takashi Ineyama、Kunisuke Izawa

  DOI：10.1016/j.jfluchem.2005.12.010

  日期：2006.5

  A facile method for the synthesis of 3'-alpha-fluoro-2',3'-dideoxyadenosine 6 has been developed. Fluorination of 5'-O-acetyl-3'-beta-bromo-3'-deoxyadenosine 3 with MOST gave 2'-beta-bromo-3'-alpha-fluoro-2',3'-dideoxyadenosine 4 via a rearrangement of the 3'-beta-brornine to the 2'-beta position during 3'-alpha fluorination. The 2'-beta bromine was reduced by radical reduction and then the 5'-O-acetyl group was removed to afford 3'-alpha-fluoro-2',3'-dideoxyadenosine 6 in good yield. A possible mechanism for the rearrangement is discussed. (C) 2006 Elsevier B.V. All rights reserved.