Mizuno Y, Tsuchida K, Tampo H
Nucleic Acids Symp Ser. 1982(11):45-8.
Among many attempts toward the total synthesis of Sinefungin one of the most promising approach was found to be the transglycosylation of the amino acid-D-ribofuranosyl portion of 15 to N6-acyladenine. The key intermediate (15) was prepared from uridine in 12 steps. Thus, treatment of 2',3'-O-isopropylidene-uridine 5'-aldehyde (5) with methyl 4-nitrobutanoate gave rise to an aldol adduct (6) which was led to 4-nitro-4-(5'-deoxy-2', 3'-O-isopropylideneuridin-5'-yl)-butanal (10) via 8. A four-component condensation involving 10 afforded N,N-disubstituted alpha-aminocarboxamide derivative (11). The transglycosylation involving 8 and N6-benzoyladenine was successfully achieved. A parallel transglycosylation involving 15 and N6-benzoyladenine is under way to obtain 16.
在众多全合成西奈芬净的尝试中，最有前景的方法之一是将15的氨基酸-D-核糖呋喃糖部分与N6-酰基腺嘌呤进行转糖基化反应。关键中间体（15）由尿苷经12步反应制备而成。因此，用4-硝基丁酸甲酯处理2',3'-O-异丙叉基-尿苷5'-醛（5）得到醛醇加合物（6），其经8转化为4-硝基-4-(5'-脱氧-2',3'-O-异丙叉基尿苷-5'-基)-丁醛（10）。涉及10的四组分缩合反应得到N,N-二取代的α-氨基甲酰胺衍生物（11）。涉及8和N6-苯甲酰腺嘌呤的转糖基化反应成功实现。涉及15和N6-苯甲酰腺嘌呤的平行转糖基化反应正在进行中以得到16。
