1-(3-deoxy-3-fluoro-2,5-di-O-trityl-β-D-xylofuranosyl)uracil | 129885-89-8

• 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: 1-(3-deoxy-3-fluoro-2,5-di-O-trityl-β-D-xylofuranosyl)uracil
• 英文别名: 1-(3-deoxy-3-fluoro-2,5-bis-O-triphenylmethyl-β-D-xylofuranosyl)uracil；1-[(2R,3S,4S,5R)-4-fluoro-3-trityloxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 129885-89-8
• 化学式: C₄₇H₃₉FN₂O₅
• 分子量: 730.835
• InChiKey: RHSZJQJNARIYIQ-XWRSFLHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  55
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-deoxy-3-fluoro-2,5-di-O-trityl-β-D-xylofuranosyl)uracil 在 溶剂黄146 作用下， 反应 6.0h， 以62%的产率得到1-(3-deoxy-3-fluoro-β-D-xylofuranosyl)uracil
  参考文献：
  名称：

  Diethylaminosulfur trifluoride (DAST) as a fluorinating agent of pyrimidine nucleosides having a 2',3'-vicinal diol system.

  摘要：

  通过使用二乙基三氟化硫（DAST），研究了用氟原子置换具有邻位二醇体系的嘧啶核苷中的羟基的问题。虽然碱基的参与往往会阻碍氟原子的引入，但研究发现，对碱基和/或糖基进行适当的修饰可以实现所需的氟脱羟基反应，从而以良好的收率得到 5'-、3'-β 和 2'-α 氟化尿嘧啶核苷。

  DOI：

  10.1248/cpb.38.1136
• 作为产物：
  描述：

  二乙胺基三氟化硫 、 2',5'-di-O-trityluridine 生成 1-(3-deoxy-3-fluoro-2,5-di-O-trityl-β-D-xylofuranosyl)uracil
  参考文献：
  名称：

  HAYAKAWA, HIROYUKI;TAKAI, FUMI;TANAKA, HIROMICHI;MIYASAKA, TADASHI;YAMAGU+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1136-1139

  摘要：

  DOI：

文献信息

• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• HAYAKAWA, HIROYUKI;TAKAI, FUMI;TANAKA, HIROMICHI;MIYASAKA, TADASHI;YAMAGU+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1136-1139
  作者：HAYAKAWA, HIROYUKI、TAKAI, FUMI、TANAKA, HIROMICHI、MIYASAKA, TADASHI、YAMAGU+

  DOI：——

  日期：——
• NUCLEOSIDE DERIVATIVES FOR THE TREATMENT OF HEPATITIS C
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1315736A2

  公开（公告）日：2003-06-04
• [EN] NUCLEOSIDE DERIVATIVES<br/>[FR] DERIVES DE NUCLEOSIDES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002018404A2

  公开（公告）日：2002-03-07

  Use of compounds of formula (I), wherein R1 is hydrogen, hydroxy, alkyl, hydroxyalkyl, alkoxy, halogen, cyano, isocyano or azido; R2 is hydrogen, hydroxy, alkoxy, chlorine, bromine or iodine; R3 is hydrogen; or R?2 and R3¿ together represent =CH¿2?; or R?2 and R3¿ represent fluorine; X is O, s or CH¿2?; a, b, c, d denoting asymmetric carbon atoms each of which is substituted with 4 different substituents; and B signifies a purine base B1 which is connected through the 9-nitrogen of formula (B1), wherein R?4¿ is hydrogen, hydroxyl, alkyl, alkoxy, alkylthio, aryloxy, arylthio, heterocyclyl, NR7R8, halogen or SH; R5 is hydrogen, hydroxy, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, heterocyclyl, heterocyclylamino, halogen, NR?7R8, NHOR9, NHNR7R8¿ or SH; R6 is hydrogen, hydroxy, alkyl, alkoxy, alkylthio, aryloxy, arylthio, heterocyclyl, NR7R8, halogen, SH or cyano; R?7 and R8¿ are independently of each other hydrogen, alkyl, aryl, hydroxyalkyl, alkenylalkyl, alkynylalkyl, cycloalkyl or acyl; R9 is hydrogen, alkyl or aryl; or B signifies an oxidised purine base B2 which is connected through the 9-nitrogen of formula (B2), wherein R?4, R5 and R6¿ are as defined above; or B signifies a purine base B3 which is connected through the 9-nitrogen of formula (B3), wherein R?4 and R6¿ are as defined above; R10 is hydrogen, alkyl or aryl; Y is O, S or NR11; R11 is hydrogen, hydroxy, alkyl, OR9, heterocyclyl or NR?7R8; R7, R8 and R9¿ are as defined above; or B signifies a pyrimidine base B4 which is connected through the 1-nitrogen of formula (B4), wherein Z is O or S; R12 is hydrogen, hydroxy, alkyl, alkoxy, haloalkyl, alkylthio, aryl, aryloxy, arylthio, heterocyclyl, heterocyclylamino, halogen, NR?7R8, NHOR9, NHNR7R8¿ or SH; R13 is hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, cycloalkyl or halogen; R?7, R8 and R9¿ are as defined above; or B signifies a pyrimidine base B5 which is connected through the 1-nitrogen of formula (B5), wherein Y, Z, R10 are as defined above for the treatment of diseases mediated by the Hepatitis C Virus (HIV) or for the preparation of a medicament for such treatment. The invention is concerned with novel and known purine and pyrimidine nucleoside derivatives, their use as inhibitors of subgenomic Hepatitis C Virus (HCV) RNA replication and pharmaceutical compositions of such compounds.
• Diethylaminosulfur trifluoride (DAST) as a fluorinating agent of pyrimidine nucleosides having a 2',3'-vicinal diol system.
  作者：Hiroyuki HAYAKAWA、Fumi TAKAI、Hiromichi TANAKA、Tadashi MIYASAKA、Kentaro YAMAGUCHI

  DOI：10.1248/cpb.38.1136

  日期：——

  Displacement of a hydroxyl group in pyrimidine nucleosides having a vicinal diol system by a fluorine atom was investigated by using diethylaminosulfur trifluoride (DAST). Though participation of the base moiety often thwarts the desired introduction of a fluorine atom, it was found that appropriate modification of the base and/or sugar moieties allowed the desired fluorodehydroxylation to occur, giving 5'-, 3'-β-, and 2'-α-fluorinated uracilnucleosides in good yields.

  通过使用二乙基三氟化硫（DAST），研究了用氟原子置换具有邻位二醇体系的嘧啶核苷中的羟基的问题。虽然碱基的参与往往会阻碍氟原子的引入，但研究发现，对碱基和/或糖基进行适当的修饰可以实现所需的氟脱羟基反应，从而以良好的收率得到 5'-、3'-β 和 2'-α 氟化尿嘧啶核苷。