[(2R,3R,4R,5R)-5-[(1R)-2-amino-1-hydroxy-2-oxoethyl]-2-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]-4-methoxyoxolan-3-yl] acetate | 1384271-35-5

• 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: [(2R,3R,4R,5R)-5-[(1R)-2-amino-1-hydroxy-2-oxoethyl]-2-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]-4-methoxyoxolan-3-yl] acetate
• CAS: 1384271-35-5
• 化学式: C₂₁H₂₅N₃O₉
• 分子量: 463.444
• InChiKey: GSNVHXYLQDLBBC-HGJKNBTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-[(1R)-2-amino-1-hydroxy-2-oxoethyl]-2-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]-4-methoxyoxolan-3-yl] acetate 在 甲酸 、 palladium on activated charcoal 、 氢气 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.0h， 以99%的产率得到[(2R,3R,4R,5R)-5-[(1R)-2-amino-1-hydroxy-2-oxoethyl]-2-(2,4-dioxopyrimidin-1-yl)-4-methoxyoxolan-3-yl] acetate
  参考文献：
  名称：

  A reliable Pd-mediated hydrogenolytic deprotection of BOM group of uridine ureido nitrogen

  摘要：

  The benzyloxymethyl (BOM) group has been utilized widely in syntheses of a variety of natural and non-natural products. The BOM group is also one of few choices to protect uridine ureido nitrogen. However, hydrogenolytic cleavage of the BOM group of uridine derivatives has been unreliably performed via heterogeneous conditions using Pd catalysts. One of the undesirable by-products formed by Pd-mediated hydrogenation conditions is the over-reduced product in which the C5-C6 double bond of the uracil moiety was saturated. To date, we have generated a wide range of uridine-containing antibacterial agents, where the BOM group has been utilized in their syntheses. In screening of deprotection conditions of the BOM group of uridine ureido nitrogen under Pd-mediated hydrogenation conditions, we realized that the addition of water to the (PrOH)-Pr-i-based hydrogenation conditions can suppress the formation of over-reduced uridine derivatives and the addition of HCO2H (0.5%) dramatically improve the reaction rate. An optimized hydrogenation condition described here can be applicable to the BOM-deprotections of a wide range of uridine derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.035