(1'R,4'S)-9-<4-benzyloxymethylcyclopent-2-enyl>-6-(2-methoxyethoxy)-9H-purin-2-amine | 133397-50-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1'R,4'S)-9-<4-benzyloxymethylcyclopent-2-enyl>-6-(2-methoxyethoxy)-9H-purin-2-amine
• 英文别名: (1'R,4'S)-9-(4-benzyloxymethylcyclopent-2-enyl)-6-(2-methoxyethoxy)-9H-purin-2-amine；6-(2-methoxyethoxy)-9-[(1R,4S)-4-(phenylmethoxymethyl)cyclopent-2-en-1-yl]purin-2-amine
• CAS: 133397-50-9
• 化学式: C₂₁H₂₅N₅O₃
• 分子量: 395.461
• InChiKey: DYEDTWHEPKBQMD-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1'R,4'S)-9-<4-benzyloxymethylcyclopent-2-enyl>-6-(2-methoxyethoxy)-9H-purin-2-amine 在 甲醇 、 aluminium(III) iodide 、 三氟化硼乙醚 、 氨 作用下， 以 乙腈 为溶剂， 反应 3.67h， 生成 (-)-卡巴韦
  参考文献：
  名称：

  Total synthesis of (–)-carbovir

  摘要：

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).

  DOI：

  10.1039/p19910002479
• 作为产物：
  描述：

  6-O-(methoxyethyl)guanine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 乙二醇甲醚 、 水 、 三正丁基氢锡 、 lithium hydride 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 (1'R,4'S)-9-<4-benzyloxymethylcyclopent-2-enyl>-6-(2-methoxyethoxy)-9H-purin-2-amine
  参考文献：
  名称：

  Total synthesis of (–)-carbovir

  摘要：

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).

  DOI：

  10.1039/p19910002479

文献信息

• [EN] SYNTHESIS OF CYCLOPENTENE DERIVATIVES
  申请人：GLAXO GROUP LIMITED

  公开号：WO1991001318A1

  公开（公告）日：1991-02-07

  (EN) A process is described for the preparation of the 1R-cis isomer of carbovir, [1'R,4'S]-2-amino-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-1,9-dihydro-6H-purin-one and its physiologically acceptable salts from a compound of formula (II) (where L represents a leaving group, R1 represents a hydrogen atom or a hydroxyl protecting group and R2 represents OH, NH2 or a protected hydroxyl group). The 1R-cis isomer of carbovir is an antiviral agent with potent activity against human immunodeficiency virus (HIV).(FR) On décrit un procédé de préparation de l'isomère 1R-cis de carbovire, le [1'R,4'S]-2-amino-9-[4-(hydroxyméthyl)-2-cyclopentène-1-yle]-1,9-dihydro-6H-purin-one et ses sels physiologiquement acceptables, à partir d'un composé dont la formule est (II), (où L représente un groupe de sortie, R1 représente un atome d'hydrogène ou un groupe protecteur d'hydroxyle et R2 représente OH, NH2 ou un groupe hydroxyle protégé). L'isomère 1R-cis de carbovire est un agent antiviral à activité puissante contre le virus de l'immunodéficience humaine (HIV).
• Total synthesis of (–)-carbovir
  作者：Martin F. Jones、Peter L. Myers、Colin A. Robertson、Richard Storer、Christopher Williamson

  DOI：10.1039/p19910002479

  日期：——

  Optically pure (-)-carbovir has been prepared by two different routes involving stereospecific opening of chiral cyclopentene epoxides by substituted purines. Introduction of the 2',3' unsaturation was accomplished by mesylate elimination, either after introduction of the purine (Route 1), or earlier in the sequence, producing a novel vinyl epoxide (Route 2).