3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose | 197647-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose
• 英文别名: 3-deoxy-3-fluoro-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-5-thio-α-D-glucofuranose；[(2R)-2-[(3aR,5S,6R,6aS)-6-fluoro-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-acetylsulfanylethyl] acetate
• CAS: 197647-11-3
• 化学式: C₁₃H₁₉FO₆S
• 分子量: 322.355
• InChiKey: FQMZCQWCQKTZBR-IYKVGLELSA-N

物化性质

• 熔点：
  101-103 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  385.0±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose 在 三氟乙酸 作用下， 反应 0.5h， 以66%的产率得到3-deoxy-3-fluoro-5-S-acetyl-6-O-acetyl-5-thio-α-D-glucofuranose
  参考文献：
  名称：

  简明合成3-氟-5-硫代木糖和吡喃葡萄糖，它们各自对应的吡喃核苷衍生物的有用前体

  摘要：

  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

  DOI：

  10.1016/j.carres.2008.02.004
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 吡啶 、 盐酸 、 potassium fluoride 、 磺酰氯 、 potassium acetate 、 溶剂黄146 、 甲基磺酰氯 、 硫脲 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙二醇甲醚 、 水 为溶剂， 生成 3-deoxy-5,6-di-O,S-acetyl-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

文献信息

• An alternative synthesis of antineoplastic 4′-thiocytidine analogue 4′-thioFAC
  作者：Yuichi Yoshimura、Mikari Endo、Shinji Sakata

  DOI：10.1016/s0040-4039(99)00048-9

  日期：1999.3

  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.
• 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.