1-(3,5-di-O-benzyl-β-D-xylofuranosyl)uracile | 118174-05-3

• 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-(3,5-di-O-benzyl-β-D-xylofuranosyl)uracile
• 英文别名: 1-(3',5'-di-O-benzyl-β-D-xylo-furanosyl)uracil；1-[(2R,3R,4R,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 118174-05-3
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: ATKQQFREKNNJFT-PSWRPDDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] acetamidosulfanylformate 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-(3,5-di-O-benzyl-β-D-xylofuranosyl)uracile
  参考文献：
  名称：

  从环状1,2-硫代碳酸盐糖中高效选择性合成糖呋喃糖基叠氮化物和核苷。

  摘要：

  [反应：见正文]环状1,2-硫代碳酸酯糖是方便的原料，用于通过区域和立体选择性硫代碳酸酯开环选择性而有效地制备糖呋喃糖基叠氮化物和核苷。

  DOI：

  10.1021/ol034975a

文献信息

• Synthèse de nucléosides pyrimidiques non protégés en O-2′ à partir de sulfites cycliques en C-1—C-2
  作者：Christian H. Gagnieu、Alain Guiller、Henri Pacheco

  DOI：10.1016/0008-6215(88)80080-6

  日期：1988.9

  was readily hydrolyzed in slightly acid conditions to give in almost quantitative yield 1-(3,5,6-tri- O -benzoyl-β- d -glucofuranosyl)uracil. This new synthetic method for nucleosides unprotected at O-2′ was also tested in other sugar series. In some cases, only the 1′,2′- trans -nucleosides were obtained, but in others, small yields (3–10%) of 1′,2′- cis -nucleosides were detected. The α-to-β ratio

  摘要在没有任何催化剂的熔融过程中，用过量的双（三甲基硅）尿嘧啶处理3,5,6-三-O-苯甲酰基-α-d-葡萄糖呋喃糖1,2-亚硫酸盐，得到了1-（-）极好的收率。 3,5,6-三-O-苯甲酰基-2-O-三甲基甲硅烷基-β-d-葡萄糖基呋喃糖基）尿嘧啶，在弱酸性条件下容易水解，几乎可以定量得到1-（3,5,6-tri -O-苯甲酰基-β-d-葡糖呋喃糖基）尿嘧啶。在其他糖系列中也测试了这种在O-2'处未保护的核苷的新合成方法。在某些情况下，仅获得了1'，2'-顺式核苷，而在其他情况下，仅检测到了1'，2'-顺式核苷的少量收率（3-10％）。α与β之比似乎取决于反应温度。2,4-二甲氧基嘧啶还与糖1,2-亚硫酸盐和4-O-甲基-1-（3,5，
• Highly β-stereoselective nucleosidation from α-d-xylo- and α-d-ribo-furanose 1,2-thiocarbonates
  作者：Rafael Robles、Concepción Rodrı́guez、Luis Álvarez de Cienfuegos、Antonio J. Mota

  DOI：10.1016/j.tetasy.2003.12.037

  日期：2004.3

  Cyclic 1,2-thiocarbonates of alpha-D-xylo- and alpha-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording beta-nucleosides with complete stereo selectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an S(N)2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl)acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1' were ascertained by chemical correlation synthesizing the corresponding 2,2'-anhydronucleosides. (C) 2004 Elsevier Ltd. All rights reserved.
• GAGNIEU, CHRISTIAN H.;GUILLER, ALAIN;PACHECO, HENRI, CARBOHYDR. RES., 180,(1988) N 2, C. 233-242
  作者：GAGNIEU, CHRISTIAN H.、GUILLER, ALAIN、PACHECO, HENRI

  DOI：——

  日期：——