3,5-二-O-苄基-α-D-呋喃核糖苷甲酯的高效合成及其在2'-C-β-烷氧基甲基尿苷合成中的应用。
Efficient synthesis of methyl 3,5-di-O-benzyl-alpha-D-ribofuranoside and application to the synthesis of 2'-C-beta-alkoxymethyluridines.
作者信息
Li Nan-Sheng, Lu Jun, Piccirilli Joseph A
机构信息
Howard Hughes Medical Institute, Department of Biochemistry and Molecular Biology, University of Chicago, 929 East 57th Street, Chicago, Illinois 60637, USA.
出版信息
Org Lett. 2007 Aug 2;9(16):3009-12. doi: 10.1021/ol071075b. Epub 2007 Jul 13.
Methyl 3,5-di-O-arylmethyl-alpha-D-ribofuranosides have been used extensively as synthons to construct 2'-C-branched ribonucleosides. Herein, we describe efficient access to methyl 3,5-di-O-arylmethyl-alpha-D-ribofuranosides (aryl: 2-ClC(6)H(4), 3-ClC(6)H(4), 4-ClC(6)H(4), 4-BrC(6)H(4), 2,4-Cl(2)C(6)H(3), Ph) in 72-82% yields from methyl D-ribofuranoside. We also demonstrate efficient access to the versatile precursor methyl 3,5-di-O-benzyl-alpha-D-ribofuranoside (3f) and the synthesis of 2'-C-beta-methoxymethyl- and 2'-C-beta-ethoxymethyluridine in six steps from 3f with overall yields of 18% and 32%, respectively.
3,5-二-O-芳基甲基-α-D-呋喃核糖苷已被广泛用作合成子来构建2'-C-支链核糖核苷。在此，我们描述了从D-呋喃核糖苷以72 - 82%的产率高效制备3,5-二-O-芳基甲基-α-D-呋喃核糖苷（芳基：2-氯苯基、3-氯苯基、4-氯苯基、4-溴苯基、2,4-二氯苯基、苯基）的方法。我们还展示了从3,5-二-O-苄基-α-D-呋喃核糖苷（3f）高效制备通用前体，并从3f经六步分别以18%和32%的总产率合成2'-C-β-甲氧基甲基尿苷和2'-C-β-乙氧基甲基尿苷的方法。
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