bis-TMS-N-acetylcytosine | 96472-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: bis-TMS-N-acetylcytosine
• 英文别名: bis(trimethylsilyl)-N-acetylcytosine；trimethylsilyl N-(2-trimethylsilyloxypyrimidin-4-yl)ethanimidate
• CAS: 96472-73-0
• 化学式: C₁₂H₂₃N₃O₂Si₂
• 分子量: 297.505
• InChiKey: SQQBCKTVVRIHAY-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±52.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-5-methoxy-1,3-oxathiolane-2-methyl-(2'(R)-hydroxy)phenyl acetate 、 bis-TMS-N-acetylcytosine 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以68%的产率得到(2R)-5-(4'-acetamido-2'-oxo-pyrimidin-1'-yl)-1,3-oxathiolane-2-methyl-(2'(R)-hydroxy)phenyl acetate
  参考文献：
  名称：

  A PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE

  摘要：

  公开号：

  EP2161267B1
• 作为产物：
  描述：

  N4-乙酰胞嘧啶 、 牛血清白蛋白 以 1,1-二氯乙烷 为溶剂， 生成 bis-TMS-N-acetylcytosine
  参考文献：
  名称：

  Homogemcitabines

  摘要：

  本发明涉及通式（2）的同质gemcitabine，其中取代基的含义如权利要求1所述，其制备方法，用于制备活性剂gemcitabin的用途以及用于制备治疗增殖性疾病药物的用途。本发明还涉及新的中间体，用于本发明方法中。

  公开号：

  US20080249119A1

文献信息

• 一种合成拉米夫定中间体的方法
  申请人：上海创诺制药有限公司

  公开号：CN104926806B

  公开（公告）日：2020-03-24

  本发明公开了一种合成拉米夫定中间体的方法，所述方法包括：使式VI所示化合物与盐酸甲醇溶液进行甲醚化反应，得到式V所示化合物；使式V所示化合物与硼氢化钠在乙醇中进行还原反应，得到式IV所示化合物；使式IV所示化合物在有机碱作用下与氯代碳酸酯进行酯化反应生成双环羧酯，得到式III所示化合物；使式III所示化合物在酸催化下与乙酸酐进行酰化反应，得到式II所示化合物；使式II所示化合物在三甲基碘硅烷的催化下与硅烷保护的N4‑乙酰氨基胞嘧啶进行糖基化反应，得到式I’所示的内消旋化合物；对I’所示的内消旋化合物进行重结晶拆分，得到式I所示的拉米夫定中间体。本发明方法具有操作简单，成本低，产物纯度高等优点。
• Stereoselective Synthesis of 1,2-<i>cis</i>-<i>N</i>-Glycosides by the<i>N</i>-Bromosuccinimide Promoted Reaction of Thioglycosides with Silylated Pyrimidme Bases
  作者：Hideyuki Sugimura、Ikuyo Muramoto、Tadashi Nakamura、Kenji Osumi

  DOI：10.1246/cl.1993.169

  日期：1993.1

  The coupling of O-benzylated 1-thioglycosides, derived from d-glucose, d-mannose, d-ribose, d-xylose, and d-arabinose, with silylated pyrimidme bases by activation with N-bromosuccinimide uniformly afforded the corresponding 1,2-cis-N-glycosides with good selectivity.

  通过N-溴代琥珀酰亚胺活化，将源自d-葡萄糖、d-甘露糖、d-核糖、d-木糖和d-阿拉伯糖的O-苄基1-硫代糖苷与硅烷化的嘧啶碱结合，可以均匀地得到具有良好选择性的相应1,2-顺式-N-糖苷。
• Stereoselective Synthesis of 2'-Deoxy-.beta.-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases
  作者：Hideyuki Sugimura、Kenji Osumi、Yasuko Kodaka、Keiko Sujino

  DOI：10.1021/jo00104a020

  日期：1994.12

  The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-alpha-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (alpha:beta = 1:24-0:1) to afford 2'-deoxy-beta-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields. The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable a form. A subsequent S(N)2 type attack to the intermediate will lead to the beta-nucleosides. By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-beta-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside. On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products. The product distribution of the regioisomers was, however, proved to change with reaction time. For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (alpha:beta = 1:2-1:4.8). The isolated yields of the 9-beta isomers after purification were acceptable for practical use.
• Synthesis of 1-(2,3-dideoxy-2-fluoro-.beta.-D-threo-pentofuranosyl)cytosine (F-ddC). A promising agent for the treatment of acquired immune deficiency syndrome
  作者：Masami Okabe、Ruen Chu Sun、Gladys B. Zenchoff

  DOI：10.1021/jo00014a013

  日期：1991.7

  A new and practical synthesis of a fluorinated analogue of 2',3'-dideoxycytidine (ddC), 1-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)cytosine (F-ddC), is described. The key feature in the synthesis is the use of the selectively protected 2,4,5-trihydroxypentanoic acid derivative 15 as a chiral pool synthon.
• Zipse, Hendrik; Artin, Erin; Wnuk, Stanislaw, Journal of the American Chemical Society, 2009, vol. 131, p. 200 - 211
  作者：Zipse, Hendrik、Artin, Erin、Wnuk, Stanislaw、Lohman, Gregory J. S.、Martino, Debora、et al.

  DOI：——

  日期：——