N2,5'-O-ditrityl-8,2'-anhydro-3'-deoxy-3'-fluoro-8-mercapto-9-β-arabinofuranosylguanine | 876728-25-5

• 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: N2,5'-O-ditrityl-8,2'-anhydro-3'-deoxy-3'-fluoro-8-mercapto-9-β-arabinofuranosylguanine
• 英文别名: (11R,12R,13R,15R)-12-fluoro-4-(tritylamino)-13-(trityloxymethyl)-14-oxa-10-thia-1,3,5,8-tetrazatetracyclo[7.6.0.02,7.011,15]pentadeca-2(7),3,8-trien-6-one
• CAS: 876728-25-5
• 化学式: C₄₈H₃₈FN₅O₃S
• 分子量: 783.926
• InChiKey: GYZPFUAVAXYUGX-YKZCYYGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  58
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N2,5'-O-ditrityl-8,2'-anhydro-3'-deoxy-3'-fluoro-8-mercapto-9-β-arabinofuranosylguanine 在 镍 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 2’,3’-二脱氧-3’-氟鸟苷
  参考文献：
  名称：

  A concise synthesis of 3′-α-fluoro-2′,3′-dideoxyguanosine (FddG) via 3′-α-selective fluorination of 8,2′-thioanhydronucleoside

  摘要：

  The antiviral nucleoside 3'-alpha-fluoro-2',3'-dideoxyguanosine (FddG) was synthesized via 3'-alpha-selective fluorination of 8,2'thioanhydronucleoside as the key step. Desulfurization of Y-alpha-fluoro-3'-deoxy-8,2'-thioanhydronucleoside could be achieved by the treatment with Raney Ni in toluene. This method provides a concise route to 3'-alpha-fluoro-2',3'-dideoxynucleosides that avoids the use of explosive and expensive SF4-related fluorinating reagents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.074
• 作为产物：
  描述：

  8,2'-anhydro-8-mercaptoguanosine 在 全氟丁基磺酰氟 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N2,5'-O-ditrityl-8,2'-anhydro-3'-deoxy-3'-fluoro-8-mercapto-9-β-arabinofuranosylguanine
  参考文献：
  名称：

  A concise synthesis of 3′-α-fluoro-2′,3′-dideoxyguanosine (FddG) via 3′-α-selective fluorination of 8,2′-thioanhydronucleoside

  摘要：

  The antiviral nucleoside 3'-alpha-fluoro-2',3'-dideoxyguanosine (FddG) was synthesized via 3'-alpha-selective fluorination of 8,2'thioanhydronucleoside as the key step. Desulfurization of Y-alpha-fluoro-3'-deoxy-8,2'-thioanhydronucleoside could be achieved by the treatment with Raney Ni in toluene. This method provides a concise route to 3'-alpha-fluoro-2',3'-dideoxynucleosides that avoids the use of explosive and expensive SF4-related fluorinating reagents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.074

文献信息

• Production method of fluorinated purine nucleoside derivative, intermediate therefor and production method thereof
  申请人：Ajinomoto Co., Inc.

  公开号：EP1816135A1

  公开（公告）日：2007-08-08

  Purine nucleosides which are fluorinated at the 3'-position (preferably the α-position), may be economically and efficiently produced by fluorinating a novel purine nucleoside derivative (1) in which the hydroxyl group at the 5'-position is protected to obtain a novel purine nucleoside derivative (2) in a high yield. The derivative (2) is subjected to desulfurization, deprotection of R1 and, as necessary protection, deprotection, or modification of nucleic acid base moiety, to obtain the desired purine nucleoside (3). wherein each symbol is as defined in the specification.

  嘌呤核苷在3'-位（最好是α-位）被氟化后，可以通过氟化一种新的嘌呤核苷衍生物（1）来经济高效地生产，其中5'-位的羟基被保护以获得高产率的新嘌呤核苷衍生物（2）。衍生物（2）经过脱硫化、去保护R1，必要时保护、去保护或修饰核酸碱基部分，以获得所需的嘌呤核苷（3）。 其中每个符号的定义如规范中所述。
• A concise synthesis of 3′-α-fluoro-2′,3′-dideoxyguanosine (FddG) via 3′-α-selective fluorination of 8,2′-thioanhydronucleoside
  作者：Takayoshi Torii、Tomoyuki Onishi、Kunisuke Izawa、Tokumi Maruyama

  DOI：10.1016/j.tetlet.2006.06.074

  日期：2006.8

  The antiviral nucleoside 3'-alpha-fluoro-2',3'-dideoxyguanosine (FddG) was synthesized via 3'-alpha-selective fluorination of 8,2'thioanhydronucleoside as the key step. Desulfurization of Y-alpha-fluoro-3'-deoxy-8,2'-thioanhydronucleoside could be achieved by the treatment with Raney Ni in toluene. This method provides a concise route to 3'-alpha-fluoro-2',3'-dideoxynucleosides that avoids the use of explosive and expensive SF4-related fluorinating reagents. (c) 2006 Elsevier Ltd. All rights reserved.