Potent and selective in vitro activity of 3'-deoxythymidin-2'-ene (3'-deoxy-2',3'-didehydrothymidine) against human immunodeficiency virus.
Potent and selective in vitro activity of 3'-deoxythymidin-2'-ene (3'-deoxy-2',3'-didehydrothymidine) against human immunodeficiency virus.
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DOI：
10.1016/0006-2952(87)90253-x
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发表时间：
1987-09
影响因子：
5.8
通讯作者：
T. Lin;R. Schinazi;W. Prusoff
中科院分区：
文献类型：
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作者：
T. Lin;R. Schinazi;W. Prusoff
3 '-脱氧胸苷-2'-烯（3 '-deoxy-2' u3 '-didehydrot~！用餐）4.将环醚（3，8.64 g，38.4 mmol）在240 ml含有8.70 g（76.4 mmol）叔丁醇钾的干燥DMSO中的溶液在室温下搅拌2小时。用几份热丙酮研磨残余物。通过过滤除去不溶性物质，并将滤液蒸发至干。将残余物通过硅胶柱洗脱（CHCl 3-EtOH，2：1），得到6.5g（76%）产物：mp 158-160; NMR（Me2SO-d 6）~ 1.82（s，3H，5-CH3），3.53（m，2H，5'-H），4.80 1H NMR（400 MHz，DMS 0-d 6）δ：4.96（t，lH，5 '-OH，D2 O可交换的），5.90（m，lH，3'-H，乙烯基），6.40（m，lH，2 '-H，乙烯基），6.82（m，lH，1'-H），7.67（s，lH，6-H）。
3'-Deoxythymidin-2'-ene (3'-deoxy-2'u3'-didehydrot~! dine) 4. A solution of the cyclic ether (3, 8.64 g, 38.4 mmol) in 240 ml of dried DMSO containing 8.70 g (76.4 mmol) of potassium t-butoxide was stirred at room temperature for 2 hr. The reaction mixture was neutralized to~ pH 7 with ethanolic acetic acid, and the solution was then evaporated to dryness at~ 50 under reduced pressure. The residue was triturated with several portions of hot acetone. The insoluble materials were removed by filtration, and the filtrate was evaporated to dryness. The residue was eluted through a silica gel column (CHCI3-EtOH, 2: 1) to yield 6.5 g (76%) of product: mp 158-160; NMR (Me2SO-d 6)~ 1.82 (s, 3H, 5-CH3), 3.53 (m, 2H, 5'-H), 4.80 (m, IH, 4'-H), 4.96 (t, IH, 5'-OH, D20 exchangeable), 5.90 (m, IH, 3'-H, vinyl), 6.40 (m, IH, 2'-H, vinyl), 6.82 (m, IH, I'-H), 7.67 (s, IH, 6-H).