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• W2003248303 endingPage "8512" @default.
• W2003248303 startingPage "8504" @default.
• W2003248303 abstract "A novel efficient method for the synthesis of locked nucleic acid (LNA) monomers is described. The LNA 5',3'-diols containing thymine, 4-N-acetyl- and 4-N-benzoylcytosine, 6-N-benzoyladenine, and 2-N-isobutyrylguanine as nucleobases were prepared via convergent syntheses. The method is based on the use of the common sugar intermediate 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose (8) that easily can be prepared from D-glucose in multigram scale. Four different nucleobases were stereoselectively coupled to 8 using a modified Vorbrüggen procedure to give the corresponding 4'-C-branched nucleoside derivatives. Subsequent ring closing furnished the protected LNA nucleosides. The 5'-O-mesyl groups were efficiently displaced by nucleophilic substitution using sodium benzoate. Saponification of the 5'-benzoates followed by catalytic removal of the 3'-O-benzyl groups afforded the free LNA diols. The exocyclic amino groups of adenosine and cytidine were selectively acylated to give 4-N-acetyl- or 4-N-benzoyl-LNA-C and 6-N-benzoyl-LNA-A. The isobutyryl group of guanine was retained during the preparation of 2-N-isobutyryl-LNA-G. The LNA-T diol and base-protected LNA diols can be directly converted into LNA-phosphoramidites for automated chemical synthesis of LNA containing oligonucleotides." @default.
• W2003248303 created "2016-06-24" @default.
• W2003248303 creator A5015208487 @default.
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• W2003248303 date "2001-11-15" @default.
• W2003248303 modified "2023-10-14" @default.
• W2003248303 title "A Simplified and Efficient Route to 2‘-<i>O</i>, 4‘-<i>C</i>-Methylene-Linked Bicyclic Ribonucleosides (Locked Nucleic Acid)" @default.
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• W2003248303 doi "https://doi.org/10.1021/jo010732p" @default.
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