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Literature DB >> 17929936

syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides.

Gang Cheng¹, Renhua Fan, Jesús M Hernández-Torres, Fabien P Boulineau, Alexander Wei.

Abstract

The syn-selective addition of organozinc compounds to 4alpha-epoxypyranosides (4alpha-EPs), generated from methyl beta-D-glucoside or aminoglucoside, provides an efficient route to pyranosides with alpha-L-ido configurations, including L-iduronic acid, neosamine B, and higher monosaccharide derivatives.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2007 PMID： 17929936 PMCID： PMC2597405 DOI： 10.1021/ol702185y

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

17 in total

Review 1. Synthesis and reactions of unsaturated sugars.

Authors: Robert J Ferrier; John O Hoberg
Journal: Adv Carbohydr Chem Biochem Date: 2003 Impact factor: 12.200

2. Nucleophilic catalysis of the iodine-zinc exchange reaction: preparation of highly functionalized diaryl zinc compounds.

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Journal: Angew Chem Int Ed Engl Date: 2004-02-13 Impact factor: 15.336

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Journal: Adv Carbohydr Chem Biochem Date: 1974 Impact factor: 12.200

5. Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides.

Authors: Shouquan Huo
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

Review 6. The structures of Escherichia coli O-polysaccharide antigens.

Authors: Roland Stenutz; Andrej Weintraub; Göran Widmalm
Journal: FEMS Microbiol Rev Date: 2006-05 Impact factor: 16.408

7. Silver(I)-catalyzed addition of zirconocenes to glycal epoxides. A new synthesis of alpha-C-glycosides.

Authors: Peter Wipf; Joshua G Pierce; Nian Zhuang
Journal: Org Lett Date: 2005-02-03 Impact factor: 6.005

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Authors: J D Parrish; R Daniel Little
Journal: Org Lett Date: 2002-05-02 Impact factor: 6.005

9. Mirror-image carbohydrates: synthesis of the unnatural enantiomer of a blood group trisaccharide.

Authors: Fabien P Boulineau; Alexander Wei
Journal: J Org Chem Date: 2004-05-14 Impact factor: 4.354

10. Functionalized arylzinc compounds in ethereal solvent: direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides.

Authors: Ryo Ikegami; Akiko Koresawa; Takanori Shibata; Kentaro Takagi
Journal: J Org Chem Date: 2003-03-21 Impact factor: 4.354

4 in total