Literature DB >> 21070063

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

David Crich1, Indrajeet Sharma.   

Abstract

α-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.

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Year:  2010        PMID： 21070063      PMCID： PMC3064765          DOI： 10.1021/jo101453y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  34 in total

1.  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

2.  Chemistry of 1-Alkoxy-1-glycosyl Radicals: The Manno- and Rhamnopyranosyl Series. Inversion of alpha- to beta-Pyranosides and the Fragmentation of Anomeric Radicals.

Authors:  David Crich; Sanxing Sun; Jarmila Brunckova
Journal:  J Org Chem       Date:  1996-01-26       Impact factor: 4.354

3.  Electrostatic interactions in cations and their importance in biology and chemistry.

Authors:  Deborah M Smith; K A Woerpel
Journal:  Org Biomol Chem       Date:  2006-02-27       Impact factor: 3.876

4.  Stereoselective formation of glycosyl sulfoxides and their subsequent equilibration: ring inversion of an alpha-xylopyranosyl sulfoxide dependent on the configuration at sulfur.

Authors:  David Crich; Jan Mataka; Lev N Zakharov; Arnold L Rheingold; Donald J Wink
Journal:  J Am Chem Soc       Date:  2002-05-29       Impact factor: 15.419

5.  IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE.

Authors:  David Crich; Abhisek Banerjee; Wenju Li; Qingjia Yao
Journal:  J Carbohydr Chem       Date:  2005       Impact factor: 1.667

6.  alpha-selective sialylations at -78 degrees C in nitrile solvents with a 1-adamantanyl thiosialoside.

Authors:  David Crich; Wenju Li
Journal:  J Org Chem       Date:  2007-09-07       Impact factor: 4.354

7.  Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3)- beta-D-Rha-(1-->4)-beta-D-Glu-OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652.

Authors:  David Crich; Qingjia Yao
Journal:  J Am Chem Soc       Date:  2004-07-07       Impact factor: 15.419

8.  Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors:  David Crich; Tianshun Hu; Feng Cai
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354

9.  Synthesis of 2-(4-aminophenyl)ethyl 3-deoxy-5-O-(3,4,6-tri-O-beta-D- glucopyranosyl-alpha-D-glucopyranosyl)-alpha-D-manno-oct-2-ulopyrano sid onic acid, a highly branched pentasaccharide corresponding to structures found in lipopolysaccharides from Moraxella catarrhalis.

Authors:  K Ekelöf; S Oscarson
Journal:  Carbohydr Res       Date:  1995-12-20       Impact factor: 2.104

10.  Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides.

Authors:  David Crich; Baolin Wu
Journal:  Org Lett       Date:  2008-08-21       Impact factor: 6.005
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  10 in total

1.  Synthesis of lacto-N-tetraose.

Authors:  Kelly M Craft; Steven D Townsend
Journal:  Carbohydr Res       Date:  2017-02-11       Impact factor: 2.104

Review 2.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

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.  Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors.

Authors:  Rashad R Karimov; Derek S Tan; David Y Gin
Journal:  Chem Commun (Camb)       Date:  2017-05-30       Impact factor: 6.222

6.  Stereoselective C-glycoside formation with 2-O-benzyl-4,6-O-benzylidene protected 3-deoxy gluco- and mannopyranoside donors: comparison with O-glycoside formation.

Authors:  Myriame Moumé-Pymbock; David Crich
Journal:  J Org Chem       Date:  2012-10-11       Impact factor: 4.354

7.  Dissecting the mechanisms of a class of chemical glycosylation using primary ¹³C kinetic isotope effects.

Authors:  Min Huang; Graham E Garrett; Nicolas Birlirakis; Luis Bohé; Derek A Pratt; David Crich
Journal:  Nat Chem       Date:  2012-07-22       Impact factor: 24.427

8.  Synthetic Neoglycoconjugates of Hepta- and Nonamannoside Ligands for Eliciting Oligomannose-Specific HIV-1-Neutralizing Antibodies.

Authors:  Matteo Cattin; Jean-François Bruxelle; Kurtis Ng; Markus Blaukopf; Ralph Pantophlet; Paul Kosma
Journal:  Chembiochem       Date:  2022-02-11       Impact factor: 3.461

9.  The influence of acceptor nucleophilicity on the glycosylation reaction mechanism.

Authors:  S van der Vorm; T Hansen; H S Overkleeft; G A van der Marel; J D C Codée
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

10.  A minimalist approach to stereoselective glycosylation with unprotected donors.

Authors:  Kim Le Mai Hoang; Jing-Xi He; Gábor Báti; Mary B Chan-Park; Xue-Wei Liu
Journal:  Nat Commun       Date:  2017-10-27       Impact factor: 14.919
  10 in total

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