1,2,3-tri-O-acetyl-5-deoxy-5-fluoro-β-D-ribofuranose | 149115-31-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3-tri-O-acetyl-5-deoxy-5-fluoro-β-D-ribofuranose
• 英文别名: tri-O-acetyl-5-fluoro-5-deoxy-β-D-ribofuranose；Tri-O-acetyl-5-fluor-5-desoxy-β-D-ribofuranose；[(2S,3S,4R,5S)-4,5-diacetyloxy-2-(fluoromethyl)oxolan-3-yl] acetate
• CAS: 149115-31-1
• 化学式: C₁₁H₁₅FO₇
• 分子量: 278.234
• InChiKey: ZPMKLVJPAIKLDU-GWOFURMSSA-N

物化性质

• 沸点：
  334.5±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-5-deoxy-5-fluoro-β-D-ribofuranose 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 (2R,3R,4S,5S)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(fluoromethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Probing the molecular determinants of fluorinase specificity

  摘要：

  用5'-氯-5'-脱氧腺苷（5'-ClDA）类似底物探究氟化酶酶特异性的结构决定因素，产生了具有改进和新活性的氟化酶。

  DOI：

  10.1039/c6cc09213f
• 作为产物：
  描述：

  5-fluoro-5-deoxyribose 、 乙酸酐 在 吡啶 作用下， 生成 1,2,3-tri-O-acetyl-5-deoxy-5-fluoro-β-D-ribofuranose
  参考文献：
  名称：

  5-Deoxy-5-fluoro-D-ribofuranosyl Derivatives of Certain Purines, Pyrimidines and 5,6-Dimethylbenzimidazole

  摘要：

  DOI：

  10.1021/ja01553a061

文献信息

• 5'-substituted-ribofuranosyl benzimidazoles as antiviral agents
  申请人：——

  公开号：US20030119762A1

  公开（公告）日：2003-06-26

  The present invention relates to polysubstituted benzimidazoles, having the following formula: 1 wherein Q is a substituted benzimidazole group attached at the benzimidazole 1-position; R is a halogen of atomic number 9 to 53, inclusive (i.e., —F, —Cl, —Br, or —I); azido (i.e., —N 3 ); or —X—R 1 , wherein X is a chalcogen of atomic number 8 to 16, inclusive (i.e., —O— or —S—), and R 1 may be straight or branched chain alkyl of 1 to 8 carbon atoms; and R 2 and R 3 may be the same or different and are separately —O—C(═O)CH 3 (i.e., —OAc) or hydroxy (i.e., —OH); and pharmaceutically acceptable salts and operative combinations thereof. Also provided by this invention are compositions comprising a polysubstituted benzimidazole as defined above and methods of use thereof.

  本发明涉及具有下式的多取代苯并咪唑： 1 其中 Q 是连接在苯并咪唑 1 位上的取代苯并咪唑基团；R 是原子序数为 9 至 53（含）的卤素（即 -F、-Cl、-Br 或 -I）；叠氮（即 -N 3 ）；或 -X-R 1 其中 X 是原子序数为 8 至 16（包括 8 和 16）的缩醛（即 -O- 或 -S-），而 R 1 可以是 1 至 8 个碳原子的直链或支链烷基；以及 R 2 和 R 3 可以相同或不同，并分别为-O-C(═O)CH 3 (即-OAc)或羟基(即-OH)；以及药学上可接受的盐及其作用组合。本发明还提供了包含如上定义的多取代苯并咪唑的组合物及其使用方法。
• Some intramolecular rearrangements when pentofuranoses are treated with diethylaminosulphur trifluoride (DAST)
  作者：A.E. Lloyd、P.L. Coe、R.T. Walker、O.W. Howarth

  DOI：10.1016/s0022-1139(00)80038-x

  日期：1993.2

  Treatment of methyl 2,3-O-isopropylidene-beta-D-ribofuranoside with DAST gave a good yield of 2,3-O-isopropylidene-5-0-methyl-beta-D-ribofuranosyl fluoride in which the methoxy group had migrated from C-1 --> C-5 and been replaced with retention of configuration by fluorine. The corresponding aldehyde when treated under similar conditions underwent a similar migration to give 5-deoxy-5-fluoro-2,3-O-isopropylidene-5-O-methyl-beta-D-ribofuranosyl fluoride. A similar migration occurred with methyl 2',3'-di-O-acetyl-beta-D-ribofuranoside and with acetyl 2,3-O-isopropylidene-D-ribofuranose but not with 1,2,3-tri-O-acetyl-D-ribofuranose. Thus the migration depends upon the migratory aptitude of the substituent at C-1 and the conformation of the furanose ring. Two ribofuranosyl fluorides were used as starting materials from which to make nucleosides by the method of Noyori and Hayoshi.
• Synthesis and Antiviral Activity of Certain 5‘-Modified Analogs of 2,5,6-Trichloro-1-(β-<scp>d</scp>-ribofuranosyl)benzimidazole
  作者：Kristjan S. Gudmundsson、John C. Drach、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm9604888

  日期：1997.2.1

  A series of 5'-modified 2,5,6-trichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpesviruses and for cytotoxicity. The 5'-methoxy, 5'-ethoxy, and 5'-butoxy analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were prepared by coupling the appropriate 5-O-alkyl-1,2,3-tri-O-acetyl-beta-D-ribose derivatives with 2,5,6-trichlorobenzimidazole followed by removal of the protecting groups. The 5'-deoxy-5'-fluoro, -5'-chloro, -5'-bromo, -5'-iodo, -5'-azido, and -5'-thiomethyl derivatives were synthesized in a similar fashion. All of these 5'-modified derivatives had significant activity against HCMV in plaque and yield reduction assays (IC50's = 0.5-14.2 mu M) but had little activity (IC50's > 100 mu M) against HSV-1. This pattern is similar to the antiviral activity profile observed for TCRB. The 5'-halogenated derivatives were more active than the other 5'-modified derivatives with antiviral activity well separated from cytotoxicity. In general, cytotoxicity of all the 5'-modified derivatives was greater in human foreskin fibroblasts (HFF cells) than in L1210 or K-B tumor cells. These results indicate that the viral target tolerates significant modifications of TCRB at the 5'-position without adversely affecting activity against HCMV, whereas the 5'-modifications increased cytotoxicity in human diploid cells.
• 5'-SUBSTITUTED-RIBOFURANOSYL BENZIMIDAZOLES AS ANTIVIRAL AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP0845001A1

  公开（公告）日：1998-06-03
• US5589467A
  申请人：——

  公开号：US5589467A

  公开（公告）日：1996-12-31