An unusual solvent effect on the regiochemical outcome (N-9 versus N-7) of guanine glycosylation using Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine)

Autor: Adrian Wai-Hing Cheung, Lisa M. Garofalo, Robert Alan Goodnow, Achyutharao Sidduri
Rok vydání: 2000
Předmět:
Zdroj: Tetrahedron Letters. 41:3303-3307
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00423-8
Popis: An unexpectedly low N-9/N-7 regioselectivity was obtained when Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine) was coupled with a d -glucosamine derivative under trimethylsilyl trifluoromethanesulfonate activation. An unprecedented solvent effect (toluene versus dichloroethane) on the N-9/N-7 ratio was also observed in the same study. The use of 2-N-acetyl-6-O-benzylguanine to successfully overcome the above regioselectivity problem is described.
Databáze: OpenAIRE