(3R,4S)-3-tert-Butoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopentanone | 848750-10-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,4S)-3-tert-Butoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopentanone
• 英文别名: (3S,4R)-3-[tert-butyl(diphenyl)silyl]oxy-4-[(2-methylpropan-2-yl)oxymethyl]cyclopentan-1-one
• CAS: 848750-10-7
• 化学式: C₂₆H₃₆O₃Si
• 分子量: 424.656
• InChiKey: MQPIUFOAIKSVMM-YKSBVNFPSA-N

物化性质

• 沸点：
  475.0±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-tert-Butoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopentanone 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 L-Selectride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 生成 (1S,2R,4S)-4-(6-chloropurin-9-yl)-2-(tert-butoxymethyl)cyclopentanol
  参考文献：
  名称：

  5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin

  摘要：

  A straightforward synthesis of (1S,2R,3R,4R)-4-(6-aminopurin-9-yl)-2-hydroxymethylcyclopentane-1,3-diol (2), an isomer of aristeromycin, and its 2'-deoxy derivative 3 from readily available disubstituted cyclopentenes is presented. An antiviral analysis of 2 showed it to have significant activity versus Epstein-Barr virus (IC50 0.62 mug/mL in the Elisa assay) and to be free of cytotoxicity effects against the host cells. In a much less comprehensive antiviral analysis, 3 also was active towards Epstein-Barr (IC50 7.58 mug/mL in the Elisa assay) but this was accompanied by cellular toxicity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.016
• 作为产物：
  描述：

  甲基叔丁基醚 、 4(S)-<(tert-butyldiphenylsilyl)oxy>cyclopent-2-en-1-one 在 copper(I) bromide dimethylsulfide complex 、 2,2'-硫代二丙烷 potassium tert-butylate 、 仲丁基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以87%的产率得到(3R,4S)-3-tert-Butoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopentanone
  参考文献：
  名称：

  5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin

  摘要：

  A straightforward synthesis of (1S,2R,3R,4R)-4-(6-aminopurin-9-yl)-2-hydroxymethylcyclopentane-1,3-diol (2), an isomer of aristeromycin, and its 2'-deoxy derivative 3 from readily available disubstituted cyclopentenes is presented. An antiviral analysis of 2 showed it to have significant activity versus Epstein-Barr virus (IC50 0.62 mug/mL in the Elisa assay) and to be free of cytotoxicity effects against the host cells. In a much less comprehensive antiviral analysis, 3 also was active towards Epstein-Barr (IC50 7.58 mug/mL in the Elisa assay) but this was accompanied by cellular toxicity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.016

文献信息

• 5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin
  作者：Xue-qiang Yin、Stewart W. Schneller

  DOI：10.1016/j.tet.2004.12.016

  日期：2005.2

  A straightforward synthesis of (1S,2R,3R,4R)-4-(6-aminopurin-9-yl)-2-hydroxymethylcyclopentane-1,3-diol (2), an isomer of aristeromycin, and its 2'-deoxy derivative 3 from readily available disubstituted cyclopentenes is presented. An antiviral analysis of 2 showed it to have significant activity versus Epstein-Barr virus (IC50 0.62 mug/mL in the Elisa assay) and to be free of cytotoxicity effects against the host cells. In a much less comprehensive antiviral analysis, 3 also was active towards Epstein-Barr (IC50 7.58 mug/mL in the Elisa assay) but this was accompanied by cellular toxicity. (C) 2005 Elsevier Ltd. All rights reserved.