(1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol | 192118-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol
• 英文别名: (3aR,4R,6S,6aS)-2,2-dimethyl-6-[(2-methylpropan-2-yl)oxymethyl]-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 192118-38-0
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: KWLNDANQZQEFIH-ZRUFSTJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol 在 18-冠醚-6 、 sodium hydride 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (1'S,2'R,3'S,4'S)-9-<4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-yl>adenine
  参考文献：
  名称：

  Chiral Synthesis of Carbocyclic Analogues of l-ribofuranosides

  摘要：

  DOI：

  10.1021/jo9812330
• 作为产物：
  描述：

  甲基叔丁基醚 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol
  参考文献：
  名称：

  Chiral Synthesis of Carbocyclic Analogues of l-ribofuranosides

  摘要：

  DOI：

  10.1021/jo9812330

文献信息

• Asymmetric Synthesis and Antiviral Activities of <scp>l</scp>-Carbocyclic 2‘,3‘-Didehydro-2‘,3‘-dideoxy and 2‘,3‘-Dideoxy Nucleosides
  作者：Peiyuan Wang、Beth Gullen、M. Gary Newton、Yung-Chi Cheng、Reymond F. Schinazi、Chung K. Chu

  DOI：10.1021/jm9901327

  日期：1999.8.1

  syntheses of L-carbocyclic 2',3'-didehydro-2',3'-dideoxy- and 2',3'-dideoxypyrimidine and purine nucleoside analogues were accomplished, and their anti-HIV and anti-HBV activities were evaluated. The key intermediate, (1S, 4R)-1-benzoyloxy-4-(tert-butoxymethyl)cyclopent-2-ene (7), was prepared by benzoylation of the alcohol 2, selective deprotection of the isopropylidene group of 3, followed by thermal elimination

  完成了L-碳环2'，3'-didehydro-2'，3'-二脱氧-氧和2'，3'-二脱氧嘧啶和嘌呤核苷类似物的不对称合成，并评估了它们的抗HIV和抗HBV活性。关键中间体（1S，4R）-1-苯甲氧基-4-（叔丁氧基甲基）环戊-2-烯（7）是通过对醇2进行苯甲酰化而制备的，对3的异亚丙基进行选择性脱保护，然后通过环状原酸酯进行热消除或通过环状硫代碳酸酯进行脱氧。还通过从保护的核苷经由环原酸酯进行热消除而合成了目标化合物。发现L-碳环2'，3'-didehydro-2'，3'-二脱氧腺苷（34）表现出有效的抗HBV活性（EC（50）= 0.9 microM）和中等的抗HIV活性（EC（50 ）= 2。
• Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2′,3′-didehydro-2′,3′-dideoxyadenosine
  作者：Peiyuan Wang、Raymond F. Schinazi、Chung K. Chu

  DOI：10.1016/s0960-894x(98)00278-9

  日期：1998.7

  Asymmetric synthesis of L-carbocyclic 2',3'-didehydro-2',3'-dideoxyadenosine and its analogs were accomplished and their anti-HIV activities were evaluated. It was found that L-carbocyclic 2',3'-didehydro-2',3'-dideoxyadenosine exhibited moderately potent anti-HIV (EC50 = 2.4 microM) activity in human PBM cells without cytotoxicity up to 100 microM.

  完成了L-碳环2'，3'-didehydro-2'，3'-二脱氧腺苷及其类似物的不对称合成，并评估了它们的抗HIV活性。发现L-碳环2'，3'-didehydro-2'，3'-二脱氧腺苷在人PBM细胞中表现出中等有效的抗-HIV（EC50 = 2.4 microM）活性，而对细胞的毒性最高至100 microM。
• Solid Phase Synthesis of Carbocyclic <scp>l</scp>-2‘-Deoxynucleosides
  作者：Hyunah Choo、Youhoon Chong、Chung K. Chu

  DOI：10.1021/ol015783n

  日期：2001.5.1

  [GRAPHICS]Carbocyclic L-2 ' deoxynucleosides 17 were synthesized on solid phase in four steps from the appropriately protected intermedate 11, The Mitsunobu reaction was used as a condensation method between the carbocyclic moiety and heterocyclic bases. The regioselectivity of the carbocyclic nucleosides was compared between the solid and solution phase syntheses.
• Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides
  作者：Peiyuan Wang、Luigi A. Agrofoglio、M. Gary Newton、Chung K. Chu

  DOI：10.1016/s0040-4039(97)00898-8

  日期：1997.6

  Asymmetric synthesis of L-carbocyclic nucleosides, (+)-beta-L-aristeromycin (11) and its thymine analog (12) was accomplished. The key intermediate 3 was synthesized by a regioselective conjugate addition to the enone 1 followed by DIBAL-H reduction. Coupling of 4 with heterocycle or construction of heterocyle by a linear approach gave 11 and 12. This is the first asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides. (C) 1997 Elsevier Science Ltd.