Tetrahedron Letters p. 3859 - 3862 (1985)
Update date:2022-09-26
Topics: Protection Thymidine Uridine One-step
Claesen, C. A. A.
Pistorius, A. M. A.
Tesser, G. I.
Unprotected thymidine and uridine react with 4-nitrophenylsulfonyl ethene (3) in a base catalyzed Michael type addition to give O4-(4-nitrophenylsulfonylethyl)thymidine (6) and -uridine (7), respectively.The 4-nitrophenylsulfonylethyl group is cleaved within 2.5 hours at 50-55 deg C by concentrated aqueous ammonia, via β-elimination.
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