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)
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. (C) 2000 Elsevier Science Ltd.
Cheung, Adrian Wai-Hing,Sidduri, Achyutharao,Garofalo, Lisa M.,Goodnow Jr., Robert A.
Get Best Price for189829-34-3Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester