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One-step protection of the nucleoside base in thymidine and uridine

✍ Scribed by C.A.A. Claesen; A.M.A. Pistorius; G.I. Tesser

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 221 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)89270-9

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✦ Synopsis

Unprotected thymidine and uridine react with 4-nitrophenylsulfonyl ethene (1) in a base catalyzed Michael type addition to give 04-(4-nitrophenylsulfonylethyl)thymidine

(5) and -uridine (21, respectively. The 4-nitrophenylsulfonylethyl group is cleaved within 2.5 hours at 5D-55OC by concentrated aqueous ammonia, via B-elimination.

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