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)

被引：10

作者：

Cheung, AWH ^{[1
]}

Sidduri, A ^{[1
]}

Garofalo, LM ^{[1
]}

Goodnow, RA ^{[1
]}

机构：

[1] Hoffmann La Roche Inc, Roche Res Ctr, Nutley, NJ 07110 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)00423-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. All rights reserved.

引用

页码：3303 / 3307

页数：5

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