Literature DB >> 27942674

Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot.

Mithila D Bandara1, Jagodige P Yasomanee1, Nigam P Rath1, Christian M Pedersen2, Mikael Bols2, Alexei V Demchenko1.   

Abstract

A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.

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Year:  2017        PMID: 27942674      PMCID: PMC5496005          DOI: 10.1039/c6ob02498j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  22 in total

1.  A programmable one-pot oligosaccharide synthesis for diversifying the sugar domains of natural products: a case study of vancomycin.

Authors:  Thomas K Ritter; Kwok-Kong T Mong; Haitian Liu; Takuji Nakatani; Chi-Huey Wong
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-06       Impact factor: 15.336

Review 2.  Going to extremes: "super" armed glycosyl donors in glycosylation chemistry.

Authors:  Henrik H Jensen; Christian Marcus Pedersen; Mikael Bols
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

3.  Mechanism of chemical O-glycosylation: from early studies to recent discoveries.

Authors:  Laurel K Mydock; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2009-11-12       Impact factor: 3.876

4.  Mechanisms of glycosylation reactions studied by low-temperature nuclear magnetic resonance.

Authors:  Tobias Gylling Frihed; Mikael Bols; Christian Marcus Pedersen
Journal:  Chem Rev       Date:  2015-04-29       Impact factor: 60.622

5.  Revisiting the armed-disarmed concept rationale: s-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis.

Authors:  Medha N Kamat; Alexei V Demchenko
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

6.  On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides.

Authors:  Sophon Kaeothip; Steven J Akins; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2010-08-10       Impact factor: 2.104

7.  New principles for glycoside-bond formation.

Authors:  Xiangming Zhu; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  One pot/two donors/one diol give one differentiated trisaccharide: powerful evidence for reciprocal donor-acceptor selectivity (RDAS).

Authors:  Bert Fraser-Reid; J Cristóbal López; K V Radhakrishnan; M V Nandakumar; Ana M Gómez; Clara Uriel
Journal:  Chem Commun (Camb)       Date:  2002-09-21       Impact factor: 6.222

9.  Superarming common glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

Authors:  Hemali D Premathilake; Laurel K Mydock; Alexei V Demchenko
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

10.  Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

Authors:  Swati S Nigudkar; Alexei V Demchenko
Journal:  Chem Sci       Date:  2015-05-01       Impact factor: 9.825

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  2 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  Regenerative Glycosylation.

Authors:  Yashapal Singh; Tinghua Wang; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-12-22       Impact factor: 4.354

  2 in total

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