New Synthesis of a Protected Ketonucleoside by a Non-Cryogenic Oxidation with TFAA/DMSO

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• 作者：Robert B. Appell and Robert J. Duguid
• 刊名：Organic Process Research & Development
• 出版年：2000
• 出版时间：May 2000
• 年：2000
• 卷：4
• 期：3
• 页码：172 - 174
• 全文大小：69K
• 年卷期：v.4,no.3(May 2000)
• ISSN：1520-586X

文摘

An improved synthesis of the ketonucleoside 2'-Oxo-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-cytidine (6),an intermediate in the synthesis of the potent anti-tumor agent1 (MDL 101,731 or FMdC), is reported which incorporates atrifluoroacetic acid/dimethylsulfoxide oxidation process. Thisoxidation procedure eliminates the cryogenic reaction conditionsand the necessity of protection at the N-4 amine used in thepreviously published route. Simplified isolation procedures for3 and 4 eliminate two chromatographic purification steps.Overall yields are comparable to those reported previously.