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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)

✍ Scribed by Adrian Wai-Hing Cheung; Achyutharao Sidduri; Lisa M Garofalo; Robert A Goodnow Jr.

Book ID: 104210230
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 171 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00423-8

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✦ Synopsis

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.

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ChemInform Abstract: An Unusual Solvent

ChemInform Abstract: 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).

✍ Adrian Wai-Hing Cheung; Achyutharao Sidduri; Lisa M. Garofalo; Robert A. Goodnow 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 38 KB 👁 1 views

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