5,6-anhydro-3-deoxy-3-fluoro-1,2-O-isopropylidene-β-L-ido-pentofuranose | 197647-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-anhydro-3-deoxy-3-fluoro-1,2-O-isopropylidene-β-L-ido-pentofuranose
• 英文别名: 3-deoxy-3-fluoro-5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose；(3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyl-5-[(2S)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 197647-12-4
• 化学式: C₉H₁₃FO₄
• 分子量: 204.198
• InChiKey: GQXFOIFUXVZMOC-TVNFTVLESA-N

物化性质

• 沸点：
  239.7±40.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-3-deoxy-3-fluoro-1,2-O-isopropylidene-β-L-ido-pentofuranose 在 硫脲 作用下， 以 甲醇 为溶剂， 生成 5,6-anhydro-3-deoxy-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose
  参考文献：
  名称：

  SOLID FORM OF 4'-THIO-2'-FLUORONUCLEOSIDE PHOSPHAMIDE COMPOUND AND PREPARATION METHOD THEREFOR AND USE THEREOF

  摘要：

  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。

  公开号：

  US20190241603A1
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose 在 吡啶 、 盐酸 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5,6-anhydro-3-deoxy-3-fluoro-1,2-O-isopropylidene-β-L-ido-pentofuranose
  参考文献：
  名称：

  SOLID FORM OF 4'-THIO-2'-FLUORONUCLEOSIDE PHOSPHAMIDE COMPOUND AND PREPARATION METHOD THEREFOR AND USE THEREOF

  摘要：

  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。

  公开号：

  US20190241603A1

文献信息

• A concise synthesis of 3-fluoro-5-thio-xylo- and glucopyranoses, useful precursors towards their corresponding pyranonucleoside derivatives
  作者：Evangelia Tsoukala、Stella Manta、Niki Tzioumaki、George Agelis、Dimitri Komiotis

  DOI：10.1016/j.carres.2008.02.004

  日期：2008.5

  acetylated 3-fluoro-5-thio-D-xylopyranose with silylated thymine afforded the corresponding nucleoside. Selective benzoylation and direct methanesulfonylation of 3-fluoro-1,2-O-isopropylidene-alpha-D-glucofuranose gave the 6-O-benzoyl-5-O-methylsulfonyl derivative, which on treatment with sodium methoxide afforded the 5,6-anhydro derivative. Treatment of the latter with thiourea, followed by acetolysis

  1,2,4-三-O-乙酰基-3-脱氧-3-氟-5-硫代-D-吡喃葡萄糖，1,2,4,6-四-O-乙酰基-3-脱氧-的化学合成描述了3-氟-5-硫代-α-D-吡喃葡萄糖及其胸腺嘧啶的相应核苷。通过水解3-氟-1,2-O-异亚丙基-5-S-乙酰基5-硫代-的异亚丙基进行处理的3-氟-5-S-乙酰基-5-硫代-D-木呋喃糖的处理具有甲醇氨和直接乙酰化的D-木呋喃糖导致三乙酰化的3-脱氧-3-氟-5-硫代-D-木吡喃糖。乙酰化的3-氟-5-硫代-D-吡喃吡喃糖与甲硅烷基化的胸腺嘧啶缩合得到相应的核苷。3-氟-1,2-O-异亚丙基-α-D-葡萄糖呋喃糖的选择性苯甲酰化和直接甲磺酰化得到6-O-苯甲酰基-5-O-甲基磺酰基衍生物，其经甲醇钠处理后得到5,6-无水衍生物。后者用硫脲处理，然后进行乙酰分解，得到3-氟-5-S-乙酰基-6-O-乙酰基-1,2-O-异亚丙基-5-硫代-α-D-葡糖呋喃糖。将5
• Compound of 4′-thionucleoside, as well as preparation method therefor, pharmaceutical composition thereof and application thereof
  申请人：Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.

  公开号：US10662214B2

  公开（公告）日：2020-05-26

  The present invention relates to a novel compound of 4′-thionucleoside, a preparation method therefor, a pharmaceutical composition comprising the same and an application thereof. Specifically, the present invention relates to a phosphamide derivative of 4′-thionucleoside, a preparation method therefor, a pharmaceutical composition comprising the same, a use thereof in the preparation of a medicine for preventing or treating abnormal cell proliferation diseases (for example, tumors or cancers and related diseases) or virus infectious diseases, and a method of using the same for preventing or treating abnormal cell proliferation diseases (for example, tumors or cancers and related diseases) or virus infectious diseases.

  本发明涉及一种新型的4′-硫代核苷化合物、其制备方法、包含该化合物的药物组合物及其应用。具体地说，本发明涉及一种 4′-硫代核苷的磷酰胺衍生物、其制备方法、包含该磷酰胺衍生物的药物组合物、其在制备预防或治疗异常细胞增殖疾病（例如肿瘤或癌症及相关疾病）或病毒传染性疾病的药物中的用途，以及使用该磷酰胺衍生物预防或治疗异常细胞增殖疾病（例如肿瘤或癌症及相关疾病）或病毒传染性疾病的方法。
• [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。
• Synthetic Studies on 2′-Substituted-4′-thiocytidine Derivatives as Antineoplastic Agents
  作者：Yuichi Yoshimura、Mikari Endo、Kenji Kitano、Kohei Yamada、Shinji Sakata、Shinji Miura、Haruhiko Machida

  DOI：10.1080/15257779908041569

  日期：1999.4

  As potential antineoplastic agents, we have synthesized 4'-thioFAC and 4'-thiocytarazid by developing an alternative synthetic method. 4'-ThioFAC showed potent antineoplastic activities in vivo as well as in vitro.
• An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid
  作者：Yuichi Yoshimura、Mikari Endo、Shinji Miura、Shinji Sakata

  DOI：10.1021/jo990958g

  日期：1999.10.1

  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.