Surzhikov S A
Bioorg Khim. 1994 Oct;20(10):1114-24.
A general synthetic method for 4'-hydroxymethyl-2',3'-anhydronucleosides from 1,2-O-isopropylidene-4-hydroxymethyl-alpha-D-xylofuranose is described. The condensation of 1,2-di-O-acetyl-3-O-methanesulphonyl-4-benzoyloxymethyl-5-O- benzoyl-D-xylofuranose with trimethylsilyl derivatives of N6-benzoyladenine and N2-palmitoylguanine in the presence of stannic chloride resulted in the corresponding nucleosides. After their treatment with NH4OH-EtOH, corresponding 2',3'-riboanhydronucleosides were isolated. Condensation of 1,2-di-O-acetyl-3-O-benzoyl-4-benzoyloxymethyl-5-O-benzoyl-D-xy lofuranose with trimethylsilyl derivatives of purines followed by selective deacetylation led to the nucleosides with free 2'-OH group. Their 2'-O-mesylation and epoxidering closure resulted in the isolation of 2',3'-anhydrolyxonucleosides with 38-44% yields. All the compounds synthesized did not inhibit HIV-1 reproduction in human H9 and PBL cell cultures nor HSV-2 and HCMV reproduction in vero cells up to 100 microM concentrations.
描述了一种由1,2-O-异丙叉基-4-羟甲基-α-D-木糖呋喃糖合成4'-羟甲基-2',3'-脱水核苷的通用方法。1,2-二-O-乙酰基-3-O-甲磺酰基-4-苯甲酰氧基甲基-5-O-苯甲酰基-D-木糖呋喃糖与N6-苯甲酰腺嘌呤和N2-棕榈酰鸟嘌呤的三甲基硅烷基衍生物在氯化锡存在下缩合，得到相应的核苷。用NH4OH-EtOH处理后，分离得到相应的2',3'-核糖脱水核苷。1,2-二-O-乙酰基-3-O-苯甲酰基-4-苯甲酰氧基甲基-5-O-苯甲酰基-D-木糖呋喃糖与嘌呤的三甲基硅烷基衍生物缩合，然后选择性脱乙酰化，得到具有游离2'-OH基团的核苷。它们的2'-O-甲磺酰化和环氧化反应导致以38-44%的产率分离得到2',3'-脱水木糖核苷。在高达100 microM的浓度下，所有合成的化合物在人H9和PBL细胞培养物中均不抑制HIV-1的复制，在vero细胞中也不抑制HSV-2和HCMV的复制。
