Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides

被引：9

作者：

Busscher, Guuske F. ^{[1
]}

van den Broek, Sebastiaan A. M. W. ^{[1
]}

Rutjes, Floris P. J. T. ^{[1
]}

van Delft, Floris L. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands

来源：

TETRAHEDRON | 2007年 / 63卷 / 15期

关键词：

S RIBOSOMAL-RNA; A-SITE; CRYSTAL-STRUCTURE; ANTIBIOTICS; OLIGONUCLEOTIDE; RESISTANCE; NEOMYCIN; BINDING; SPECIFICITY; TOBRAMYCIN;

D O I：

10.1016/j.tet.2007.02.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a carbohydrate mimic of 2-deoxystreptamine (2-DOS) is described starting from D-ribose. Crucial steps of the synthesis involve a stereoselective nitroaldol condensation and deoxygenation via elimination-in situ reduction. Moreover, glycosylation of the carbohydrate 2-DOS derivative with a phenyl thioglycoside donor in the presence of TTBP and AgOTf followed by ring-closing metathesis yielded a conformationally restricted aminoglycoside analogue. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3183 / 3188

页数：6

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