9-<β-D-(Tri-O-acetyl)xylopyranosyl>-1-methyl-2-(methylthio)purin-6(1H)-one | 137363-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-<β-D-(Tri-O-acetyl)xylopyranosyl>-1-methyl-2-(methylthio)purin-6(1H)-one
• 英文别名: [(3R,4S,5R,6R)-4,5-diacetyloxy-6-(1-methyl-2-methylsulfanyl-6-oxopurin-9-yl)oxan-3-yl] acetate
• CAS: 137363-12-3
• 化学式: C₁₈H₂₂N₄O₈S
• 分子量: 454.461
• InChiKey: FIRNCLVEDSYBQX-ABYLEIOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  8-Amino-9-<β-D-(tri-O-acetyl)xylopyranosyl>-1-methyl-2-(methylthio)purin-6(1H)-one 在 溶剂黄146 、 sodium nitrite 作用下， 生成 9-<β-D-(Tri-O-acetyl)xylopyranosyl>-1-methyl-2-(methylthio)purin-6(1H)-one
  参考文献：
  名称：

  A new one-step synthesis of 8-aminopurine nucleoside analogs from 6-(glycosylamino)-5-nitrosopyrimidines

  摘要：

  The reaction of 6-[[beta-D-(per-O-acetyl)glycopyranosyl]amino]-5-nitrosopyrimidines (1) with POCl3/formamide furnished 8-amino-9-[(per-O-acetyl)glycopyranosyl]purines (2) in good yield. In this reaction formamide seems to play a double role, as the source of the C(8)-amino group of the purine and as the agent responsible for the reduction of the C(5)-nitroso group of the pyrimidine to a hydroxylamino group. A mechanism which reflects this belief is presented. Chemical evidence that supports the mechanism is provided.

  DOI：

  10.1021/jo00028a031

文献信息

• The Use of Formamidine Acetate in the Traube Synthesis of 9-Glycosylpurines
  作者：M. Melguizo、M. Nogueras、A. Sánchez

  DOI：10.1055/s-1992-26144

  日期：——

  Several 9-glycopyranosylpurin-6(1H)-one derivatives, where the glycosyl moiety was xylopyranosyl, glucopyranosyl 2,3,4,6-tetra-O-acetylglycopyranosyl, or 2,3,4-tri-O-xylopyranosyl, were obtained by reaction of formamidine acetate with 5-amino-6-(glycopyranosylamino)pyrimidin-4(3H)-ones or 5-amino-6-[(per-O-acetyl)glycopyranosyl]amino}pyrimidin-4(3H)-ones, respectively. The reaction conditions were mild, such that good yields, around 60%, were obtained.

  获得了几种9-吡喃糖基嘌呤-6(1H)-酮衍生物，其中糖基部分是吡喃木糖基、吡喃葡萄糖基2,3,4,6-四-O-乙酰基吡喃糖基或2,3,4-三-O-吡喃木糖基通过乙酸甲脒与分别为5-氨基-6-(吡喃糖基氨基)嘧啶-4(3H)-酮或5-氨基-6-[(全-O-乙酰基)吡喃糖基]氨基}嘧啶-4(3H)-酮。反应条件温和，收率良好，可达60%左右。