[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(1,3-thiazol-2-yl)oxolan-2-yl]methyl acetate | 1038412-63-3

• 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: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(1,3-thiazol-2-yl)oxolan-2-yl]methyl acetate
• CAS: 1038412-63-3
• 化学式: C₁₄H₁₇NO₇S
• 分子量: 343.357
• InChiKey: NXCZRKIRAQDPIR-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 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：
  129
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  四乙酰核糖 、 2-(三甲基硅基)噻唑 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(1,3-thiazol-2-yl)oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Friedel–Crafts and modified Vorbrüggen ribosylation. A short synthesis of aryl and heteroaryl-C-nucleosides

  摘要：

  A direct coupling of aryl donor and tetra-O-acetylribose in the presence of Lewis acid led to beta-C-nucleosides in good yields. In contrast, for deactivated electron-poor aromatics, a modified Vorbruggen ribosylation reaction was investigated and successfully applied in the case of 2-trimethylsilyl-thiazole. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.105

文献信息

• Use of 2-Beta-D-ribofuranosylthiazole-4-carboxamides for the manufacture of medicaments inhibiting malignant tumors
  申请人：VIRATEK, INC.

  公开号：EP0054432A1

  公开（公告）日：1982-06-23

  The compound 2-β-D-ribofuranosylthiazole-4-carboxamide has been found to be effective in the treatment of malignant tumors in warm blooded animals, as have esters of this compound, for instance 2-(2,3,5,-tri-O-acetyl-β-D-ribofuranosyl)-thiazole-4-carboxamide and 2-(5-0-phosphoryl-β-D-ribofuranosyl)-thiazole-4-carboxamide. Disclosed also are pharmaceutical compositions containing 2-p-D-ribofuranosylthiazole-4-carboxamide or a related compound as the active ingredient; as well as processes for producing the novel compounds and compositions.

  已发现化合物 2-β-D-呋喃核糖基噻唑-4-甲酰胺可有效治疗温血动物的恶性肿瘤，该化合物的酯类也是如此，例如 2-(2,3,5,-三-O-乙酰基-β-D-呋喃核糖基)-噻唑-4-甲酰胺和 2-(5-0-磷酸基-β-D-呋喃核糖基)-噻唑-4-甲酰胺。 还公开了含有 2-对-D-呋喃核糖基噻唑-4-甲酰胺或相关化合物作为活性成分的药物组合物；以及生产新型化合物和组合物的工艺。