cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopent-2-ene | 210162-81-5

• 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: cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopent-2-ene
• 英文别名: tert-butyl N-[(1S,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]-N-hydroxycarbamate
• CAS: 210162-81-5
• 化学式: C₁₅H₂₀N₆O₃
• 分子量: 332.362
• InChiKey: XPIJRPPOKSIAMW-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopent-2-ene 在 乙酰氯 作用下， 以 甲醇 为溶剂， 以100%的产率得到N-[(1S,4R)-4-(6-Amino-purin-9-yl)-cyclopent-2-enyl]-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：

  (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol 在 偶氮二甲酸二苄酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopent-2-ene
  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.