2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3(2H)-thioxo-1,2,4-triazin-5(4H)-one | 29725-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3(2H)-thioxo-1,2,4-triazin-5(4H)-one
• 英文别名: 3-thioxo-2-(tri-O-acetyl-β-D-ribofuranosyl)-3,4-dihydro-2H-[1,2,4]triazin-5-one；1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-2-thio-6-azauracil；2-Thio-6-aza-uridin-triacetat；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-oxo-3-sulfanylidene-1,2,4-triazin-2-yl)oxolan-2-yl]methyl acetate
• CAS: 29725-42-6
• 化学式: C₁₄H₁₇N₃O₈S
• 分子量: 387.37
• InChiKey: OHFWDWWWABZRBH-OJAKKHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3(2H)-thioxo-1,2,4-triazin-5(4H)-one 反应 0.33h， 以30%的产率得到Acetic acid (5aR,7R,8R,8aS)-7-acetoxymethyl-2-oxo-5a,7,8,8a-tetrahydro-2H-furo[2',3':4,5]thiazolo[3,2-b][1,2,4]triazin-8-yl ester
  参考文献：
  名称：

  A novel simple pyrolytic approach towards anhydronucleosides

  摘要：

  An interesting novel gas phase thermal intramolecular substitution reaction was discovered which led to the conversion of the 2-beta-D-N-glucosyl. 2-beta-D-N-Plactosyl and 2-beta-D-N-ribosyl derivatives of 3-thioxo-2.3-dihydro-1.2.4-triazin-5(4H)-ones into their corresponding 3,2'-anhydro-beta-D-marmosyl, 3,2'-anhydro-beta-D-talosyl and 3,2'-anhydro-beta-D-arabinosyl derivatives. The structures of these new anhydroglycosyls were determined by NMR experiments and by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.050
• 作为产物：
  描述：

  6-杂氮-2-硫脲嘧啶 、 四乙酰核糖 在 硫酸氢铵 、 六甲基二硅氮烷 、 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3(2H)-thioxo-1,2,4-triazin-5(4H)-one
  参考文献：
  名称：

  A novel simple pyrolytic approach towards anhydronucleosides

  摘要：

  An interesting novel gas phase thermal intramolecular substitution reaction was discovered which led to the conversion of the 2-beta-D-N-glucosyl. 2-beta-D-N-Plactosyl and 2-beta-D-N-ribosyl derivatives of 3-thioxo-2.3-dihydro-1.2.4-triazin-5(4H)-ones into their corresponding 3,2'-anhydro-beta-D-marmosyl, 3,2'-anhydro-beta-D-talosyl and 3,2'-anhydro-beta-D-arabinosyl derivatives. The structures of these new anhydroglycosyls were determined by NMR experiments and by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.050

文献信息

• OGNYANIK, S. S.;GONCHARENKO, V. S., 3 KONF. MOL. UCHENYX XIM.-TEXNOL. FAK. RPI, RIGA,(1989) S. 68
  作者：OGNYANIK, S. S.、GONCHARENKO, V. S.

  DOI：——

  日期：——
• US3975374A
  申请人：——

  公开号：US3975374A

  公开（公告）日：1976-08-17