Synthesis of 2'-C-beta-fluoromethyluridine |
| |
Authors: | Dai Qing Piccirilli Joseph A |
| |
Institution: | Howard Hughes Medical Institute, Department of Biochemistry & Molecular Biology, The University of Chicago, 5841 S. Maryland Ave., MC 1028, Chicago, Illinois 60637, USA. |
| |
Abstract: | reaction: see text] 2'-C-beta-Fluoromethyluridine (17) represents both a potentially important biological agent and a tool for biochemical analysis. Here we describe the first synthesis of this compound starting from uridine. The key steps include protection of the uracil base with methoxyethoxymethyl (MEM) chloride, conversion to the corresponding 2'-C-alpha-epoxide, and regioselective opening of the oxirane ring with potassium fluoride/hydrogen fluoride. Subsequent acetylation of the 3'- and 5'-hydroxyl groups enables MEM removal using B-bromocatecholborane. Deacetylation generates the parent nucleoside, 2'-C-beta-flurormethyluridine. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|