methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside | 221552-92-7

• 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: methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside
• 英文别名: Methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-D-arabinopentofuranoside；[(2R,3S,4S)-3-benzoyloxy-4-fluoro-5-methoxythiolan-2-yl]methyl benzoate
• CAS: 221552-92-7
• 化学式: C₂₀H₁₉FO₅S
• 分子量: 390.432
• InChiKey: WUBPGNSEZZQBOT-IWRZSDRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside 在 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 ((2R,3S,4S)-3-(benzoyloxy)-5-bromo-4-fluorothiolan-2-yl)methyl benzoate
  参考文献：
  名称：

  An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid

  摘要：

  Previously, we synthesized 4'-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method far the synthesis of 4'-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the I-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a beta-anomer of 4'-thioFAC. The reaction of 2,6-diaminopurine with the I-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a beta-anomer of 4'-thioFAG, a guanine congener of 4'-thioFAC, selectively. Using a similar approach, we synthesized 4'-thiocytarazid, which was not possible using the original method.

  DOI：

  10.1021/jo990958g
• 作为产物：
  描述：

  3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose 在 盐酸 、 sodium periodate 、 三氟乙酸 作用下， 以 吡啶 为溶剂， 生成 methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside
  参考文献：
  名称：

  An alternative synthesis of antineoplastic 4′-thiocytidine analogue 4′-thioFAC

  摘要：

  We have developed an alternative method for the synthesis of 2'-modified 4'-thionucleosides. The fusion of 3,5-di-O-benzoyl-1-bromo-2-deoxy-2-fluoro-4-thio-alpha-D-arabinofuranose, prepared from 1,2:5,6-diisopropylidene-alpha-D-allofuranose, with persilylated N-4-acetylcytosine predominantly gave a beta-anomer of protected 4'-thionucleoside, which was then deprotected to give 4'-thioFAC. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00048-9

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。
• 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。
• 9-(2-DEOXY-2-FLUORO-4-THIO-BETA-D-ARABINOFURANOSYL)PURINE DERIVATIVES
  申请人：YAMASA CORPORATION

  公开号：EP0839813A1

  公开（公告）日：1998-05-06

  The present invention relates to 9-(2-deoxy-2-fluoro-4-thio-beta-D-arabinofuranosyl)purine derivatives having antiviral activity, represented by formula [I]: wherein B represents a base selected from the group consisting of purine, azapurine and deazapurine, which may be substituted with halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, alkylamino, hydroxyl, hydroxyamino, aminoxy, alkoxy, mercapto, alkylmercapto, aryl, aryloxy or cyano; and R represents a hydrogen atom or a phosphoric acid residue, and to a process for the production and use thereof.

  本发明涉及具有抗病毒活性的 9-(2-脱氧-2-氟-4-硫代-beta-D-阿拉伯呋喃糖基)嘌呤衍生物，由式[I]表示： 其中 B 代表选自嘌呤、氮杂嘌呤和去氮杂嘌呤的碱基，可被卤素、烷基、卤代烷基、烯基、卤代烯基、炔基、氨基、烷基氨基、羟基、羟基氨基、氨基氧基、烷氧基、巯基、烷基巯基、芳基、芳氧基或氰基取代；R 代表氢原子或磷酸残基，并涉及其生产和使用过程。
• 1-(2-DEOXY-2-FLUORO-4-THIO-BETA-D-ARABINOFURANOSYL)CYTOSINES
  申请人：YAMASA CORPORATION

  公开号：EP0841344A1

  公开（公告）日：1998-05-13

  The present invention relates to 1-(2-deoxy-2-fluoro-4-thio-beta-D-arabinofuranosyl)cytosines having excellent antitumor activity, represented by formula [I]: wherein R represents a hydrogen atom or a phosphoric acid residue, and to a process for the production and use thereof.

  本发明涉及具有优异抗肿瘤活性的 1-(2-脱氧-2-氟-4-硫代-beta-D-阿拉伯呋喃糖基)胞嘧啶，由式[I]表示： 其中 R 代表氢原子或磷酸残基，本发明还涉及其生产和使用过程。
• [EN] NOVEL COMPOUND OF 4'-THIONUCLEOSIDE, AS WELL AS PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION THEREOF AND APPLICATION THEREOF<br/>[FR] NOUVEAU COMPOSÉ DE 4'-THIONUCLÉOSIDE, AINSI QUE SON PROCÉDÉ DE PRÉPARATION, COMPOSITION PHARMACEUTIQUE COMPRENANT CELUI-CI ET SON APPLICATION<br/>[ZH] 4'-硫代核苷的新型化合物及其制备方法、药物组合物和应用
  申请人：SICHUAN KELUN PHARMACEUTICAL RES INST CO LTD

  公开号：WO2016155593A1

  公开（公告）日：2016-10-06

  本发明涉及4'-硫代核苷的新型化合物、其制备方法、包含其的药物组合物及其应用。具体而言，本发明涉及4'-硫代核苷的磷酰胺衍生物、其制备方法、包含其的药物组合物，其在制备预防或治疗细胞增殖异常性疾病(例如肿瘤或癌症及相关病症)或病毒感染性疾病的药物中的用途，以及其用于预防或治疗细胞增殖异常性疾病(例如肿瘤或癌症及相关病症)或病毒感染性疾病的方法。