Literature DB >> 21120713

Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis.

Hemali D Premathilake1, Alexei V Demchenko.   

Abstract

: Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing both the efficiency and yield. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. The armed-disarmed approach for chemoselective oligosaccharide synthesis is one such strategy that addresses these challenges. Herein, the significant improvements that have recently emerged in the area of chemoselective activation are discussed. These advancements have expanded the scope of the armed-disarmed methodology so that it can now be applied to a wider range of oligosaccharide sequences, in comparison to the original concept. Surveyed in this chapter are representative examples wherein these excellent innovations have already been applied to the synthesis of various oligosaccharides and glycoconjugates.

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Year:  2011        PMID: 21120713      PMCID: PMC3150466          DOI: 10.1007/128_2010_106

Source DB:  PubMed          Journal:  Top Curr Chem        ISSN: 0340-1022


  45 in total

1.  1,2-diacetals: a new opportunity for organic synthesis.

Authors:  S V Ley; D K Baeschlin; D J Dixon; A C Foster; S J Ince; H W Priepke; D J Reynolds
Journal:  Chem Rev       Date:  2001-01       Impact factor: 60.622

2.  Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries.

Authors:  P H Seeberger; W C Haase
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

3.  A Free-Energy Relationship between the Rate of Acidic Hydrolysis of Glycosides and the pK(a) of Isofagomines We thank Ib Thomsen, Xifu Liang, Steen U. Hansen and Huizhen Liu for providing us with compound samples, and the Lundbeck Foundation and Danish Natural Science Research Council (THOR programme) for financial support.

Authors:  Henrik H. Jensen; Laila Lyngbye; Mikael Bols
Journal:  Angew Chem Int Ed Engl       Date:  2001-09-17       Impact factor: 15.336

4.  One-pot oligosaccharide synthesis exploiting solvent reactivity effects.

Authors:  M Lahmann; S Oscarson
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

5.  Syntheses of anomerically phosphodiester-linked oligomers of the repeating units of the Haemophilus influenzae types c and f capsular polysaccharides.

Authors:  J Hansson; P J Garegg; S Oscarson
Journal:  J Org Chem       Date:  2001-09-21       Impact factor: 4.354

6.  Highly alpha- and beta-selective radical C-glycosylation reactions using a controlling anomeric effect based on the conformational restriction strategy. A study on the conformation-anomeric effect-stereoselectivity relationship in anomeric radical reactions.

Authors:  H Abe; S Shuto; A Matsuda
Journal:  J Am Chem Soc       Date:  2001-12-05       Impact factor: 15.419

7.  One-pot synthesis of glucosamine oligosaccharides.

Authors:  Micha Fridman; Dmitry Solomon; Shay Yogev; Timor Baasov
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

8.  Automated solid-phase synthesis of oligosaccharides.

Authors:  O J Plante; E R Palmacci; P H Seeberger
Journal:  Science       Date:  2001-02-01       Impact factor: 47.728

9.  Thioglycosides protected as trans-2,3-cyclic carbonates in chemoselective glycosylations.

Authors:  T Zhu; G J Boons
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

10.  2-(Hydroxycarbonyl)benzyl glycosides: a novel type of glycosyl donors for highly efficient beta-mannopyranosylation and oligosaccharide synthesis by latent-active glycosylation.

Authors:  K S Kim; J H Kim; Y J Lee; Y J Lee; J Park
Journal:  J Am Chem Soc       Date:  2001-09-05       Impact factor: 15.419

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  6 in total

1.  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

2.  Streamlined access to carbohydrate building blocks: Methyl 2,4,6-tri-O-benzyl-α-d-glucopyranoside.

Authors:  Ganesh Shrestha; Gustavo A Kashiwagi; Keith J Stine; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2021-11-26       Impact factor: 2.104

3.  Studies on the selectivity between nickel-catalyzed 1,2-cis-2-amino glycosylation of hydroxyl groups of thioglycoside acceptors with C2-substituted benzylidene N-phenyl trifluoroacetimidates and intermolecular aglycon transfer of the sulfide group.

Authors:  Fei Yu; Hien M Nguyen
Journal:  J Org Chem       Date:  2012-08-09       Impact factor: 4.354

4.  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

5.  Probing the influence of protecting groups on the anomeric equilibrium in sialic acid glycosides with the persistent radical effect.

Authors:  Pavan K Kancharla; Takayuki Kato; David Crich
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419

6.  2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis.

Authors:  Hemali D Premathilake; Alexei V Demchenko
Journal:  Beilstein J Org Chem       Date:  2012-04-18       Impact factor: 2.883

  6 in total

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