1-(5-O-Methoxycarbonyl-3-desoxy-3-dithiomethoxycarbonylamino-methansulfonyl-β-D-arabinofuranosyl)-uracil | 18353-91-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(5-O-Methoxycarbonyl-3-desoxy-3-dithiomethoxycarbonylamino-methansulfonyl-β-D-arabinofuranosyl)-uracil
• 英文别名: [1-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-O²-methanesulfonyl-O⁵-methoxycarbonyl-β-D-1-deoxy-arabinofuranos-3-yl]-dithiocarbamic acid methyl ester
• CAS: 18353-91-8
• 化学式: C₁₄H₁₉N₃O₉S₃
• 分子量: 469.518
• InChiKey: QUOLTLAZBZFGPM-CZULRBLNSA-N

反应信息

• 作为反应物：
  描述：

  1-(5-O-Methoxycarbonyl-3-desoxy-3-dithiomethoxycarbonylamino-methansulfonyl-β-D-arabinofuranosyl)-uracil 在 吡啶 作用下， 生成 1-<5-O-Methoxycarbonyl-2,3-dideoxy-(2'-methylmercapto-<3,2:4',5'>Δ^2'-thiazolin)-β-D-ribofuranosyl>-uracil
  参考文献：
  名称：

  Synthesis of 2'-Deoxy-2'-thio-3'-deoxy-3'-aminouridine.

  摘要：

  A complex neighboring approach provided a successful synthesis of 2'-deoxy-2'-thio-3'-deoxy-3'-aminouridine (IX). 1-(3'-Deoxy-3'-amino-β-D-arabinofuranosyl) uracil (I) afforded, in three steps, the blocked dithiocarbamoyl mesylate (IV), which, on heating in pyridine, cyclized to the thiazoline (V), that was deblocked to VI and reduced to the thiazolidine (VII). Compound (VII) was successively treated with mercuric chloride and hydrogen sulfide to furnish the desired product (IX).

  DOI：

  10.1248/cpb.15.1503