학술논문
Large Scale Synthesis of 2'-Amino-LNA Thymine and 5-Methylcytosine Nucleosides.
Document Type
Article
Source
Subject
*THYMINE
*METHYLCYTOSINE
*NUCLEOSIDES
*PHOSPHORAMIDITES
*ORGANIC chemistry
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Language
ISSN
0022-3263
Abstract
Thymine intermediate 17 has been synthesized on a multigram scale (50 g, 70 mmol) from starting sugar 1 in 15 steps in an overall yield of 73%, with only 5 purification steps. The key thymine intermediate 18 was obtained from 17 in a single step in 96% yield, whereas the key 5-methylcytosine intermediate 20 was obtained from 17 in 2 steps in 58% yield. This highly efficient large scale route necessitates only 2 and 3 novel steps to obtain N2'-functionalized thymine and 5-mcthylcytosine amino-LNA phosphoramidites from these key intermediates, respectively. [ABSTRACT FROM AUTHOR]