1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-benzoyl-4-thio-D-arabinitol | 878384-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-benzoyl-4-thio-D-arabinitol
• 英文别名: [(2R,3S,4S)-3-benzoyloxy-4-fluorothiolan-2-yl]methyl benzoate
• CAS: 878384-17-9
• 化学式: C₁₉H₁₇FO₄S
• 分子量: 360.406
• InChiKey: UQSXZFXATJISGE-ZACQAIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-benzoyl-4-thio-D-arabinitol 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-benzoyl-4-sulfinyl-D-arabinitol
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 2‘-Fluoro-5-methyl-4‘-thioarabinouridine (4‘S-FMAU)

  摘要：

  An improved synthesis of 2'-deoxy-2'-fluoro-5-methyl-4'-thioarabinouridine (4'S-FMAU) is described. Participation of the 3'-O-benzoyl protecting group in the thiosugar precursor influenced the stereochemistry of the N-glycosylation reaction in nonpolar solvents, permitting a higher beta/alpha ratio than previously observed for similar Lewis acid catalyzed glycosylations. Conformational analysis of the nucleoside using (3)J(HH) and (3)J(HF) NMR coupling constants together with the PSEUROT program showed that it adopted a predominantly northern conformation in contrast to 2'-deoxy-2'-fluoro-5-methylarabinouridine (FMAU), whose PSEUROT conformational analysis is presented here for the first time, which showed a dominantly southeast conformation. The sharp conformational switch attained by replacing the ring heteroatom is attributed to a decrease in relevant steric and stereoelectronic effects.

  DOI：

  10.1021/jo051844+
• 作为产物：
  描述：

  (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 在 吡啶 、 四丁基氟化铵 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.75h， 生成 1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-benzoyl-4-thio-D-arabinitol
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 2‘-Fluoro-5-methyl-4‘-thioarabinouridine (4‘S-FMAU)

  摘要：

  An improved synthesis of 2'-deoxy-2'-fluoro-5-methyl-4'-thioarabinouridine (4'S-FMAU) is described. Participation of the 3'-O-benzoyl protecting group in the thiosugar precursor influenced the stereochemistry of the N-glycosylation reaction in nonpolar solvents, permitting a higher beta/alpha ratio than previously observed for similar Lewis acid catalyzed glycosylations. Conformational analysis of the nucleoside using (3)J(HH) and (3)J(HF) NMR coupling constants together with the PSEUROT program showed that it adopted a predominantly northern conformation in contrast to 2'-deoxy-2'-fluoro-5-methylarabinouridine (FMAU), whose PSEUROT conformational analysis is presented here for the first time, which showed a dominantly southeast conformation. The sharp conformational switch attained by replacing the ring heteroatom is attributed to a decrease in relevant steric and stereoelectronic effects.

  DOI：

  10.1021/jo051844+

文献信息

• SOLID FORM OF 4'-THIO-2'-FLUORONUCLEOSIDE PHOSPHAMIDE COMPOUND AND PREPARATION METHOD THEREFOR AND USE THEREOF
  申请人：SICHUAN KELUN-BIOTECH BIOPHARMACEUTICAL CO., LTD.

  公开号：US20190241603A1

  公开（公告）日：2019-08-08

  The present invention relates to a solid form of a compound of Formula (I), a method for preparing the solid form, a pharmaceutical composition comprising the solid form, and the use of the solid form in the treatment of a disease involving abnormal cell proliferation or a viral infectious disease.

  本发明涉及化合物Formula (I)的固体形式，制备该固体形式的方法，包含该固体形式的药物组合物，以及在治疗涉及异常细胞增殖或病毒感染疾病中使用该固体形式的用途。
• [EN] PROCESS FOR PREPARING SUBSTITUTED 1-O-ACYL-2-DEOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 1-O-ACYL-2-DÉSOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSES SUBSTITUÉS
  申请人：LIBRAMEDICINA INC

  公开号：WO2011074484A1

  公开（公告）日：2011-06-23

  The present invention relates to a process for preparing 1-O-acyl-2-deoxy-2-fluoro-4-thio-ƒﾀ-D-arabinofuranoses having formula I and intermediates thereof: wherein R1 represents -C(O)-C1-C6-alkyl or -C(O)-aryl; and R2 represents C1-C6-alkyl, C1-C4-perfluoroalkyl or aryl.

  本发明涉及一种制备具有I式和其中间体的1-O-酰基-2-去氧-2-氟-4-硫基-ƒﾀ-D-阿拉比呋喃糖的过程：其中R1代表-C（O）-C1-C6-烷基或-C（O）-芳基；R2代表C1-C6-烷基，C1-C4-全氟烷基或芳基。
• PROCESS FOR PREPARING SUBSTITUTED 1-O-ACYL-2-DEOXY-2-FLUORO-4-THIO-BETA-D-ARABINOFURANOSES
  申请人：Voigtländer David

  公开号：US20110152542A1

  公开（公告）日：2011-06-23

  The present invention relates to a process for preparing 1-O-acyl-2-deoxy-2-fluoro-4-thio-β-D-arabinofuranoses having formula I and intermediates thereof: wherein R 1 represents —C(O)—C 1 -C 6 -alkyl or —C(O)-aryl; and R 2 represents C 1 -C 6 -alkyl, C 1 -C 4 -perfluoroalkyl or aryl.

  本发明涉及一种制备具有式I的1-O-酰基-2-去氧-2-氟-4-硫-β-D-阿拉比呋喃糖的方法和中间体：其中R1代表—C（O）—C1-C6-烷基或—C（O）-芳基；R2代表C1-C6-烷基，C1-C4-全氟烷基或芳基。
• Process for preparing substituted 1-O-acyl-2-deoxy-2-fluoro-4-thio-ß-D-arabinofuranoses
  申请人：LibraMedicina, Inc.

  公开号：EP2388257A1

  公开（公告）日：2011-11-23

  The present invention relates to a process for preparing 1-0-acyl-2-deoxy-2-fluoro-4-thio-β-D-arabinofuranoses in which R1 represents C(O)-C1-C6-alkyl or C(O)-aryl; R2 represents C1-C6-alkyl, C1-C4-perfluoroalkyl or aryl, and also its intermediates as such.

  本发明涉及制备1-0-酰基-2-去氧-2-氟-4-硫-β-D-阿拉伯糖呋喃糖的方法，其中R1代表C(O)-C1-C6-烷基或C(O)-芳基；R2代表C1-C6-烷基，C1-C4-全氟烷基或芳基，以及其中间体。
• Process for preparing substituted 1-O-acyl-2-deoxy-2-fluoro-4-thio-beta-D-arabinofuranoses
  申请人：Libramedicina, Inc.

  公开号：EP2799432A1

  公开（公告）日：2014-11-05

  The present invention relates to a process for preparing 1-O-acyl-2-deoxy-2-ftuoro-4-thio-β-D-arabinofuranoses having formula I and intermediates thereof: wherein R1 represents -C(O)-C1-C6-alkyl or -C(O)-aryl; and R2 represents C1-C6-alkyl, C1-C4-perfluoroalkyl or aryl.

  本发明涉及一种制备具有式 I 的 1-O-acyl-2-deoxy-2-ftuoro-4-thio-β-D-arabinofuranoses 及其中间体的工艺： 其中R1代表-C(O)-C1-C6-烷基或-C(O)-芳基；R2代表C1-C6-烷基、C1-C4-全氟烷基或芳基。