HALO SUGAR NUCLEOSIDES .6. SYNTHESIS OF SOME 5'-DEOXY-5'-IODO AND 4',5'-UNSATURATED PURINE NUCLEOSIDES

被引：41
|
作者：
DIMITRIJEVICH, SD [1 ]
VERHEYDEN, JPH [1 ]
MOFFATT, JG [1 ]
机构：
[1] SYNTEX RES CORP, INST MOLEC BIOL, PALO ALTO, CA 94304 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 03期
关键词：
D O I：
10.1021/jo01317a019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions of the 5''-hydroxyl groups of suitably substituted purine nucleosides with methyltriphenoxyphosphonium iodide in nonpolar solvents such as tetrahydrofuran and dichloromethane give the corresponding 5''-deoxy-5''-iodo nucleosides in high yield. Previously, N3,5''-cyclonucleosides were the major products of these reactions when DMF [dimethylformamide] was used as solvent. Efficient syntheses of 9-(5-deoxy-.beta.-D-erythro-pent-4-enofuranosyl) purine nucleosides are described via dehydrohalogenation of various 5''-deoxy-5''-iodoinosine, -guanosine, and -adenosine derivatives with either silver fluoride in pyridine or 1,5-diazabicyclo[4.3.0]non-5-ene in DMF or pyridine.
引用
收藏
页码：400 / 406
页数：7
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