2-amino-6-chloro-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine | 35085-24-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-6-chloro-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine
• 英文别名: 2-Amino-6-chloro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine；6-Chloro-9-[2,3,5-tris-O-(phenylmethyl)-b-D-arabinofuranosyl]-9H-purin-2-amine；9-[(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-6-chloropurin-2-amine
• CAS: 35085-24-6
• 化学式: C₃₁H₃₀ClN₅O₄
• 分子量: 572.063
• InChiKey: NDKRMXITLFLKAP-JVYBIVSJSA-N

物化性质

• 沸点：
  774.4±70.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷；甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine 在 sodium hydroxide 、 三氯化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 9-Β-D-糖呋喃鸟嘌呤
  参考文献：
  名称：

  2'-脱氧-6-硫代鸟苷，的一种方便的合成ARA -鸟嘌呤，阿糖胞苷-6-硫鸟嘌呤和某些相关嘌呤核苷通过立体有择钠盐的糖基化过程†

  摘要：

  使用立体特异性钠盐糖基化方法已经完成了生物学上重要的2'-脱氧-6-硫鸟嘌呤（11），ara -6-硫鸟嘌呤（16）和ara G（17）的简单且高收率的合成。6-氯-和2-氨基-6-氯嘌呤（分别为1和2）的钠盐与1-氯-2-脱氧-3,5-二-O-（对甲苯甲酰基）-α-的糖基化D-赤型-五呋喃糖（3）给出了相应的N-9取代核苷，它们是具有β-端基异构体构型的主要产物（4和5，以及少量的N-7位置异构体（6和7）。在含有甲醇钠的甲醇中用硫化氢处理4，以93％的收率得到2'-deoxy-6-thioinosine（10）。类似地，将5以71％的产率转化为2'-脱氧-6-硫鸟苷（β-TGdR，11）。2的钠盐与1-氯-2,3,5-三-O-苄基-α-D-阿拉伯呋喃糖（8）的反应分别得到N-7和N-9糖基化产物13和9。9的脱苄基作用用三氯化硼在-78°下用62％的收率得到通用的中间体2-氨基-6-氯

  DOI：

  10.1002/jhet.5570250653
• 作为产物：
  描述：

  1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 在 盐酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 147.0h， 生成 2-amino-6-chloro-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine
  参考文献：
  名称：

  Stereoselective synthesis of 9-β-d-arabianofuranosyl guanine and 2-amino-9-(β-d-arabianofuranosyl)purine

  摘要：

  9- beta- D -Arabian ofuranosyl guanine (6) and 2-amino-9-(beta-D-arabianofuranosyl)purine (8) were prepared from 2-amino-6-chloro-9-(2,3,5-triphenylmethoxyl-p-D-arabianofuranosyl)purine (4), a key intermediate which was stereoselectively prepared from 2,3,5-triphenylmethoxyl-D-arabianofuranose and 2-amino-6-chloro-purine. The yield of the intermediate was obviously improved and only P-isomer was formed by using the activated molecular sieve as environmental friendly catalyst, overcoming the defect that a 1: 1 mixture of alpha- and beta-isomers was formed, which was difficult to separate, when toxic mercury cyanide was previously used as catalyst. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.029

文献信息

• A convenient synthesis of 2′-deoxy-6-thioguanosine,<i>ara</i>-guanine,<i>ara</i>-6-thioguanine and certain related purine nucleosides by the stereospecific sodium salt glycosylation procedure
  作者：Naeem B. Hanna、Kandasamy Ramasamy、Roland K. Robins、Ganapathi R. Revankar

  DOI：10.1002/jhet.5570250653

  日期：1988.11

  A simple and high-yield synthesis of biologically significant 2′-deoxy-6-thioguanosine (11), ara-6-thioguanine (16) and araG (17) has been accomplished employing the Stereospecific sodium salt glycosylation method. Glycosylation of the sodium salt of 6-chloro- and 2-amino-6-chloropurine (1 and 2, respectively) with 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose (3) gave the corresponding

  使用立体特异性钠盐糖基化方法已经完成了生物学上重要的2'-脱氧-6-硫鸟嘌呤（11），ara -6-硫鸟嘌呤（16）和ara G（17）的简单且高收率的合成。6-氯-和2-氨基-6-氯嘌呤（分别为1和2）的钠盐与1-氯-2-脱氧-3,5-二-O-（对甲苯甲酰基）-α-的糖基化D-赤型-五呋喃糖（3）给出了相应的N-9取代核苷，它们是具有β-端基异构体构型的主要产物（4和5，以及少量的N-7位置异构体（6和7）。在含有甲醇钠的甲醇中用硫化氢处理4，以93％的收率得到2'-deoxy-6-thioinosine（10）。类似地，将5以71％的产率转化为2'-脱氧-6-硫鸟苷（β-TGdR，11）。2的钠盐与1-氯-2,3,5-三-O-苄基-α-D-阿拉伯呋喃糖（8）的反应分别得到N-7和N-9糖基化产物13和9。9的脱苄基作用用三氯化硼在-78°下用62％的收率得到通用的中间体2-氨基-6-氯
• HANNA, NACEM B.;RAMASAMY, KANDASAMY;ROBINS, ROLAND K.;REVANKAR, GANAPATHI+, J. HETEROCYCL. CHEM., 25,(1988) N, C. 1899-1903
  作者：HANNA, NACEM B.、RAMASAMY, KANDASAMY、ROBINS, ROLAND K.、REVANKAR, GANAPATHI+

  DOI：——

  日期：——
• Stereoselective synthesis of 9-β-d-arabianofuranosyl guanine and 2-amino-9-(β-d-arabianofuranosyl)purine
  作者：Xue-Jun Yu、Gai-Xia Li、Xiou-Xiang Qi、You-Quan Deng

  DOI：10.1016/j.bmcl.2004.11.029

  日期：2005.2

  9- beta- D -Arabian ofuranosyl guanine (6) and 2-amino-9-(beta-D-arabianofuranosyl)purine (8) were prepared from 2-amino-6-chloro-9-(2,3,5-triphenylmethoxyl-p-D-arabianofuranosyl)purine (4), a key intermediate which was stereoselectively prepared from 2,3,5-triphenylmethoxyl-D-arabianofuranose and 2-amino-6-chloro-purine. The yield of the intermediate was obviously improved and only P-isomer was formed by using the activated molecular sieve as environmental friendly catalyst, overcoming the defect that a 1: 1 mixture of alpha- and beta-isomers was formed, which was difficult to separate, when toxic mercury cyanide was previously used as catalyst. (C) 2004 Elsevier Ltd. All rights reserved.