2-(4'-azido-4'-deoxy-β-L-rhamnopyranosylamino)pyrimidine | 652173-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4'-azido-4'-deoxy-β-L-rhamnopyranosylamino)pyrimidine
• 英文别名: (2S,3R,4R,5R,6S)-5-azido-6-methyl-2-(pyrimidin-2-ylamino)oxane-3,4-diol
• CAS: 652173-16-5
• 化学式: C₁₀H₁₄N₆O₃
• 分子量: 266.26
• InChiKey: MNBGLRAZWMBTDW-ABXGFROZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(4'-azido-4'-deoxy-β-L-rhamnopyranosylamino)pyrimidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 (2S,3R,4R,5R,6S)-5-Amino-6-methyl-2-(pyrimidin-2-ylamino)-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  An approach to the generation of simple analogues of the antitumour agent spicamycinThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

  摘要：

  酸性介质中芳胺的一步糖基化首次扩展到腺嘌呤衍生物，比现有反应有了相当大的改进。该方法用于制备一些含有不同碱基部分的鼠李螺霉素类似物。结果表明，这种新方法将适用于广泛的碳水化合物和芳胺，可能会产生穗霉素类似物的组合库，以更好地了解这一抗肿瘤抗生素家族的作用方式。

  DOI：

  10.1039/b307795k
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 4-azido-4-deoxy-α/β-L-rhamnopyranoside 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以69%的产率得到2-(4'-azido-4'-deoxy-β-L-rhamnopyranosylamino)pyrimidine
  参考文献：
  名称：

  An approach to the generation of simple analogues of the antitumour agent spicamycinThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

  摘要：

  酸性介质中芳胺的一步糖基化首次扩展到腺嘌呤衍生物，比现有反应有了相当大的改进。该方法用于制备一些含有不同碱基部分的鼠李螺霉素类似物。结果表明，这种新方法将适用于广泛的碳水化合物和芳胺，可能会产生穗霉素类似物的组合库，以更好地了解这一抗肿瘤抗生素家族的作用方式。

  DOI：

  10.1039/b307795k

文献信息

• An approach to the generation of simple analogues of the antitumour agent spicamycinThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
  作者：St�phane Mons、George W. J. Fleet

  DOI：10.1039/b307795k

  日期：——

  The one-step glycosylation of arylamines in acidic medium is extended to adenine derivatives for the first time, providing a considerable improvement over existing reactions. This method is used to prepare some rhamnospicamycin analogues containing different base moieties. Results suggest that this novel approach will be applicable to a wide range of carbohydrates and arylamines, possibly leading to a combinatorial library of analogues of spicamycin for the better understanding of the modes of action of this antitumour antibiotic family.

  酸性介质中芳胺的一步糖基化首次扩展到腺嘌呤衍生物，比现有反应有了相当大的改进。该方法用于制备一些含有不同碱基部分的鼠李螺霉素类似物。结果表明，这种新方法将适用于广泛的碳水化合物和芳胺，可能会产生穗霉素类似物的组合库，以更好地了解这一抗肿瘤抗生素家族的作用方式。