Literature DB >> 17007825

The use of cyclic bifunctional protecting groups in oligosaccharide synthesis--an overview.

Remy E J N Litjens1, Leendert J van den Bos, Jeroen D C Codée, Herman S Overkleeft, Gijsbert A van der Marel.   

Abstract

A historical overview is presented on stereo-directing effects of cis- and trans-fused diol protective groups used on both donor and acceptor glycosides. Attention is focused on the use of cyclic carbonates and carbamates, diacetals and acetals and finally the special case of 1,2-O-orthoesters and 1,2-O-cyanoalkylidene functionalised residues.

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Year:  2006        PMID： 17007825     DOI： 10.1016/j.carres.2006.09.002

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  13 in total

1.  Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

Authors:  David Crich; Indrajeet Sharma
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.

Authors:  David Crich; Chandrasekhar Navuluri
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

3.  Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series.

Authors:  Indrajeet Sharma; Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2012-06-07       Impact factor: 2.104

4.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

5.  Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

Authors:  Pavan K Kancharla; Chandrasekhar Navuluri; David Crich
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-13       Impact factor: 15.336

6.  β-Selective Glucosylation in the Absence of Neighboring Group Participation: Influence of the 3,4-O-Bisacetal Protecting System.

Authors:  David Crich; Venkataraman Subramanian; Thomas K Hutton
Journal:  Tetrahedron       Date:  2007-06-04       Impact factor: 2.457

7.  Is donor-acceptor hydrogen bonding necessary for 4,6-O-benzylidene-directed beta-mannopyranosylation? Stereoselective synthesis of beta-C-mannopyranosides and alpha-C-glucopyranosides.

Authors:  David Crich; Indrajeet Sharma
Journal:  Org Lett       Date:  2008-10-01       Impact factor: 6.005

8.  Probing the influence of a 4,6-O-acetal on the reactivity of galactopyranosyl donors: verification of the disarming influence of the trans-gauche conformation of C5-C6 bonds.

Authors:  Myriame Moumé-Pymbock; Takayuki Furukawa; Sujit Mondal; David Crich
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

9.  Determination of the Influence of Side-Chain Conformation on Glycosylation Selectivity using Conformationally Restricted Donors.

Authors:  Suresh Dharuman; David Crich
Journal:  Chemistry       Date:  2016-02-16       Impact factor: 5.236

10.  Electrochemical generation of glycosyl triflate pools.

Authors:  Toshiki Nokami; Akito Shibuya; Hiroaki Tsuyama; Seiji Suga; Albert A Bowers; David Crich; Jun-ichi Yoshida
Journal:  J Am Chem Soc       Date:  2007-08-14       Impact factor: 15.419
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