Large Scale Synthesis of 2鈥?Amino-LNA Thymine and 5-Methylcytosine Nucleosides

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• 作者：Andreas Stahl Madsen ; Anna S酶ndergaard J酶rgensen ; Troels Bundgaard Jensen ; Jesper Wengel
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：December 7, 2012
• 年：2012
• 卷：77
• 期：23
• 页码：10718-10728
• 全文大小：407K
• 年卷期：v.77,no.23(December 7, 2012)
• ISSN：1520-6904

文摘

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鈥?functionalized thymine and 5-methylcytosine amino-LNA phosphoramidites from these key intermediates, respectively.