✦ LIBER ✦

Trimethylsilyl derivatives of N4-Boc-cytosine and their effect on I2-mediated nucleosidation of O-MTM ethers

✍ Scribed by Yumei Huang; Subhakar Dey; Philip Garner

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 150 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02850-2

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✦ Synopsis

Mono-and bis(trimethylsilyl) derivatives of N 4 -Boc-cytosine were synthesized and characterized by 1 H NMR. Only the mono(trimethylsilyl)-N 4 -Boc-cytosine participates in the iodine-mediated nucleosidation of N-Fmoc-O-methylthiomethyl serine benzyl ester to produce the cytosine nucleoamino acid, while the bis(trimethylsilyl) derivative failed to give any product. A tentative mechanistic explanation is proposed.