3-(6-cyclopropylamino-9H-purin-9-yl)-1-N-(N-tert-butyloxycarbonylhydroxamino)propane | 210163-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-(6-cyclopropylamino-9H-purin-9-yl)-1-N-(N-tert-butyloxycarbonylhydroxamino)propane
• 英文别名: tert-butyl N-[3-[6-(cyclopropylamino)purin-9-yl]propyl]-N-hydroxycarbamate
• CAS: 210163-02-3
• 化学式: C₁₆H₂₄N₆O₃
• 分子量: 348.405
• InChiKey: YCVSJYRIFZPRES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(6-cyclopropylamino-9H-purin-9-yl)-1-N-(N-tert-butyloxycarbonylhydroxamino)propane 在 盐酸 作用下， 以 甲醇 为溶剂， 以100%的产率得到N-[3-(6-Cyclopropylamino-purin-9-yl)-propyl]-hydroxylamine; hydrochloride
  参考文献：
  名称：

  Syntheses of novel hydroxylamine carbanucleosides

  摘要：

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00359-7
• 作为产物：
  描述：

  Acetic acid 3-(6-chloro-purin-9-yl)-propyl ester 在 potassium cyanide 、 偶氮二甲酸二苄酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 37.5h， 生成 3-(6-cyclopropylamino-9H-purin-9-yl)-1-N-(N-tert-butyloxycarbonylhydroxamino)propane
  参考文献：
  名称：

  Syntheses of novel hydroxylamine carbanucleosides

  摘要：

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00359-7

文献信息

• Syntheses of novel hydroxylamine carbanucleosides
  作者：Mark J. Mulvihill、Marvin J. Miller

  DOI：10.1016/s0040-4020(98)00359-7

  日期：1998.6

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.