Dueholm K L, Motawia M S, Pedersen E B, Nielsen C, Lundt I
Department of Chemistry, Odense University, Denmark.
Arch Pharm (Weinheim). 1992 Sep;325(9):597-601. doi: 10.1002/ardp.19923250914.
Direct condensation of 2-deoxy-D-ribose (1) with mercaptans using the P4O10/H2O/Bu3N reagent in chloroform resulted in coupling at C-3 to give the anomeric mixtures of the corresponding pentopyranoses 2 and pentofuranoses 3. After acetylation with acetic anhydride in dry pyridine of these 3-alkylthio pentofuranoses, coupling with the nucleobases uracil, thymine, and cytosine in accordance with the Friedel-Crafts catalyzed silyl Hilbert-Johnson method yielded the acetylated D-erythro nucleosides 7 as anomeric mixtures, separable only by means of chromatography either before or after deprotection with ammonia. The nucleosides 8a-e were devoid of any activity against HSV-1 and HIV-1.
在氯仿中使用P4O10/H2O/Bu3N试剂，使2-脱氧-D-核糖（1）与硫醇直接缩合，导致在C-3处偶联，生成相应的戊吡喃糖2和戊呋喃糖3的端基异构体混合物。这些3-烷硫基戊呋喃糖在干燥吡啶中用乙酸酐乙酰化后，根据傅克催化的硅基希尔伯特-约翰逊方法与碱基尿嘧啶、胸腺嘧啶和胞嘧啶偶联，得到乙酰化的D-赤藓糖核苷7，为端基异构体混合物，仅通过在氨脱保护之前或之后进行色谱分离。核苷8a-e对单纯疱疹病毒1型（HSV-1）和人类免疫缺陷病毒1型（HIV-1）均无任何活性。
