5-acetoxy-2-(acetoxy)methyl-1,3-oxathiolane | 136831-65-7

• 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: 5-acetoxy-2-(acetoxy)methyl-1,3-oxathiolane
• 英文别名: (5-Acetyloxy-1,3-oxathiolan-2-yl)methyl acetate
• CAS: 136831-65-7；136891-14-0；143491-55-8
• 化学式: C₈H₁₂O₅S
• 分子量: 220.246
• InChiKey: RJDQNCIJIBLJIS-UHFFFAOYSA-N

物化性质

• 沸点：
  314.4±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙醇醛二聚体 、 1,4-二硫-2,5-二醇 、 乙酸苯酯 在 三乙胺 、 subtilisin Carlsberg 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 [(2S,5S)-5-acetoxy-1,3-oxathiolan-2-yl]methyl acetate 、 ((2R,5R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl acetate 、 5-acetoxy-2-(acetoxy)methyl-1,3-oxathiolane
  参考文献：
  名称：

  Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor

  摘要：

  An enantiopure (2R,5R)-1,3-oxathiolane was obtained using a multienzymatic cascade protocol. By employing a combination of surfactant-treated subtilisin Carlsberg and Candida antarctica lipase B, the absolute configuration of the resulting 1,3-oxathiolane ring was efficiently controlled, resulting in an excellent enantiomeric excess (> 99%). This enantiopure 1,3-oxathiolane derivative is a key precursor to anti-HIV agents, such as lamivudine, through subsequent N-glycosylation.

  DOI：

  10.1016/j.mcat.2019.02.013

文献信息

• DIHETEROCYCLIC TRIAZINONE NUCLEOSIDE ANALOGS AND THEIR USE FOR MEDICATION
  申请人：Xu Lifeng

  公开号：US20210292347A1

  公开（公告）日：2021-09-23

  This invention relates to novel of formula I that are useful for the treatment, prevention and/or amelioration of human diseases of cancers. This invention also relates with their pharmaceutical compositions, preparative General Methods and applications.

  这项发明涉及一种新型的化学式I，用于治疗、预防和/或改善人类癌症等疾病。这项发明还涉及它们的药物组合物、制备一般方法和应用。
• Preparation of intermediates useful in the synthesis of antiviral nucleosides
  申请人：——

  公开号：US20030162992A1

  公开（公告）日：2003-08-28

  The present invention is an efficient process for the manufacture of &agr;-acyloxyacetaldehyde, a key intermediate in the synthesis of 1,3-oxathiolane and 1,3-dioxolane nucleosides.

  本发明是一种制备&agr;-酰氧基乙醛的高效过程，该化合物是合成1,3-噻二环己烷和1,3-二氧杂环己烷核苷的关键中间体。
• Modified nucleosides for the treatment of viral infections and abnormal cellullar proliferation
  申请人：Stuyver Lieven

  公开号：US20110269707A1

  公开（公告）日：2011-11-03

  The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  本公开发明涉及一种用于治疗Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括甲型和乙型流感）或Paramyxoviridae（包括RSV）感染或与异常细胞增殖相关的条件的组合物和方法，适用于宿主，包括动物，特别是人类，使用通式（I）-（XXIII）的核苷或其药学上可接受的盐或前药。本发明还提供了一种有效的过程，用于定量病毒载量，特别是BVDV、HCV或西尼罗河病毒载量，在宿主中使用实时聚合酶链反应（“RT-PCR”）。此外，本发明还揭示了探针分子，可以与样品中存在的病毒数量成比例地发出荧光。
• 5-halo-5-deoxy sorbopyranose compounds
  申请人：MCNEILAB, INC.

  公开号：EP0869131A1

  公开（公告）日：1998-10-07

  The present invention relates to a method of preparing BCH-189 and various analogues of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, β-BCH-189 and related compounds. Furthermore, the stereochemistry at the nucleoside 4'-position can be controlled to produce enantiomerically-enriched β-BCH-189 and its analogues.

  本发明涉及一种利用廉价前体制备 BCH-189 和 BCH-189 各种类似物的方法，并可根据需要引入官能团。这种合成路线可以立体选择性地制备这些化合物的生物活性异构体--β-BCH-189 和相关化合物。此外，还可以控制核苷 4'- 位的立体化学，从而制备出对映体丰富的 β-BCH-189 及其类似物。
• Method and compositions for the synthesis of bch-189 and related compounds
  申请人：EMORY UNIVERSITY

  公开号：EP1772151A2

  公开（公告）日：2007-04-11

  The present invention relates to a method of preparing BCH-189 and various analogues of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, β-BCH-189 and related compounds. Furthermore, the stereochemistry at the nucleoside 4'-position can be controlled to produce enantiomerically-enriched β-BCH-189 and its analogues.

  本发明涉及一种利用廉价前体制备 BCH-189 和 BCH-189 各种类似物的方法，并可根据需要引入官能团。这种合成路线可以立体选择性地制备这些化合物的生物活性异构体--β-BCH-189 和相关化合物。此外，还可以控制核苷 4'- 位的立体化学，从而制备出对映体丰富的 β-BCH-189 及其类似物。