(1S,4R,5S)-3-<(benzyloxy)methyl>-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol | 169191-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,4R,5S)-3-<(benzyloxy)methyl>-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol
• 英文别名: (1S,4R,5S)-3-[(Benzyloxy)methyl]-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol；(1S,2S,5R)-5-[(2-methylpropan-2-yl)oxy]-4-(phenylmethoxymethyl)cyclopent-3-ene-1,2-diol
• CAS: 169191-14-4
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: YNEYMXBIUQRJIQ-HRCADAONSA-N

物化性质

• 沸点：
  408.6±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4R,5S)-3-<(benzyloxy)methyl>-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol 在 咪唑 、 ammonium hydroxide 、 三氢化钐 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 三氯化硼 、 sodium hydride 、 三苯基膦 、 mercury dichloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 93.59h， 生成 (1R,2S,4S,5S)-1-hydroxymethyl-2-hydroxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxy Aristeromycin Built on a Bicyclo[3.1.0]hexane Template

  摘要：

  A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2'-deoxyaristeromycin. The X-ray structure and H-1 NMR analysis confirmed the exclusive North [2'-exo ((2)E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity.

  DOI：

  10.1080/07328319608002382
• 作为产物：
  描述：

  三甲基铝 、 (3aR,6S,6aS)-2,2-dimethyl-4-(phenylmethoxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-ol 以 二氯甲烷 、 甲苯 为溶剂， 以54%的产率得到(1S,4R,5S)-3-<(benzyloxy)methyl>-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxy Aristeromycin Built on a Bicyclo[3.1.0]hexane Template

  摘要：

  A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2'-deoxyaristeromycin. The X-ray structure and H-1 NMR analysis confirmed the exclusive North [2'-exo ((2)E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity.

  DOI：

  10.1080/07328319608002382

文献信息

• Conformationally locked nucleoside analogues
  申请人：The United States of America as represented by the Department of Health

  公开号：US05629454A1

  公开（公告）日：1997-05-13

  Conformationally locked 4',6'-cyclopropane-fused carbocyclic nucleoside analogues. The compounds are prepared by condensing a cyclopropane-fused carbocyclic allylic alcohol with substituted purine or pyrimidine bases. The condensation products are then modified to produce the adenosine, guanosine, cytidine, thymidine and uracil nucleoside analogues. The compounds are therapeutically useful as antimetabolites, or in the preparation of anti-metabolic agents.

  这段话的中文翻译如下： 构象锁定的4'，6'-环丙烷融合的碳环核苷类似物。该化合物是通过将环丙烷融合的碳环丙烯醇与取代嘌呤或嘧啶碱基缩合而制备的。缩合产物然后被改性以产生腺苷，鸟苷，胞苷，胸腺嘧啶和尿嘧啶核苷类似物。该化合物在治疗上是有用的抗代谢物，或用于制备抗代谢剂。
• CONFORMATIONALLY LOCKED NUCLEOSIDE ANALOGUES
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0720604B1

  公开（公告）日：1997-11-19
• US5629454A
  申请人：——

  公开号：US5629454A

  公开（公告）日：1997-05-13
• US5869666A
  申请人：——

  公开号：US5869666A

  公开（公告）日：1999-02-09