Hansen H B, Pedersen E B, Vestergaard B F
Department of Chemistry, Odense University, Denmark.
Arch Pharm (Weinheim). 1992 Aug;325(8):491-7. doi: 10.1002/ardp.19923250808.
The primary hydroxy group of ethyl 2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside (1) was selectively protected and the secondary hydroxy group was deoxygenated via the dithiocarbonate 3 from which ethyl 6-O-(4-methoxybenzoyl)-2,3,4-trideoxy-alpha-D-glycero-hex-2-eno pyranoside (4) and its regioisomer (5) were produced. These were converted into didehydro nucleosides by glycosylation of silylated heterocyclic bases in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst. The configurations of the anomeric products were assigned by 1H-NMR analysis of the corresponding saturated compounds which were obtained by hydrogenation of the double bond in the carbohydrate moiety. The compounds 9a,b,d, 10a,b, 14a,b,e,f, and 15a,b,e,f did not show any significant activity against HIV or HSV-1.
2,3-二脱氧-α-D-赤藓糖己-2-烯吡喃糖苷（1）的伯羟基被选择性保护，仲羟基通过二硫代碳酸酯3脱氧，由此制得6-O-(4-甲氧基苯甲酰基)-2,3,4-三脱氧-α-D-甘油己-2-烯吡喃糖苷（4）及其区域异构体（5）。在三甲基甲硅烷基三氟甲磺酸酯作为催化剂存在的情况下，通过使硅烷化的杂环碱进行糖基化反应，将它们转化为双脱氢核苷。通过对碳水化合物部分双键氢化得到的相应饱和化合物进行1H-NMR分析，确定了异头产物的构型。化合物9a、b、d、10a、b、14a、b、e、f和15a、b、e、f对HIV或HSV-1均未显示出任何显著活性。
