Literature DB >> 11975598

Preparation of alpha-C-glycosides from glycals.

J D Parrish1, R Daniel Little.   

Abstract

[reaction: see text]. A novel approach to simple C-glycosides is reported. Reductive ring opening of 1,2-anhydro sugars with titanocene(III) chloride produces an anomeric radical that can be trapped with a variety of agents. The reaction stereospecifically affords alpha-glycosides and produces a free C-2 hydroxyl group allowing for further elaboration.

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Year:  2002        PMID: 11975598     DOI: 10.1021/ol025575a

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


  5 in total

1.  The Reaction of β,γ-Epoxy Alcohols with Titanium(III) Reagents. A Proposed Role for Intramolecular Hydrogen Bonding.

Authors:  Sven Klare; Jonathan P Gordon; Andreas Gansäuer; T V RajanBabu; William A Nugent
Journal:  Tetrahedron       Date:  2019-10-01       Impact factor: 2.457

2.  Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

Authors:  Laura Alberch; Gang Cheng; Seung-Kee Seo; Xuehua Li; Fabien P Boulineau; Alexander Wei
Journal:  J Org Chem       Date:  2011-03-18       Impact factor: 4.354

3.  Synthesis of β-C-galactosyl D- and L-alanines.

Authors:  V Narasimharao Thota; Jacquelyn Gervay-Hague; Suvarn S Kulkarni
Journal:  Org Biomol Chem       Date:  2012-10-28       Impact factor: 3.876

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

Authors:  Gang Cheng; Renhua Fan; Jesús M Hernández-Torres; Fabien P Boulineau; Alexander Wei
Journal:  Org Lett       Date:  2007-10-12       Impact factor: 6.005

5.  Synthesis of C-acyl furanosides via the cross-coupling of glycosyl esters with carboxylic acids.

Authors:  Yongliang Wei; Jenny Lam; Tianning Diao
Journal:  Chem Sci       Date:  2021-07-23       Impact factor: 9.825

  5 in total

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