Literature DB >> 24963885

Organoboron-catalyzed regio- and stereoselective formation of β-2-deoxyglycosidic linkages.

Thomas M Beale1, Patrick J Moon, Mark S Taylor.   

Abstract

A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.

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Year:  2014        PMID： 24963885     DOI： 10.1021/ol501711v

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


  14 in total

1.  Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

Authors:  Yongho Park; Kaid C Harper; Nadine Kuhl; Eugene E Kwan; Richard Y Liu; Eric N Jacobsen
Journal:  Science       Date:  2017-01-13       Impact factor: 47.728

Review 2.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

3.  Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor.

Authors:  Zhitong Zheng; Liming Zhang
Journal:  Carbohydr Res       Date:  2018-10-26       Impact factor: 2.104

4.  Recent Developments in Stereoselective Chemical Glycosylation.

Authors:  Jesse Ling; Clay S Bennett
Journal:  Asian J Org Chem       Date:  2019-05-02       Impact factor: 3.319

5.  Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Authors:  Subbarao Yalamanchili; Dina Lloyd; Clay S Bennett
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

Review 6.  Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors:  Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal:  Chem Rev       Date:  2022-06-08       Impact factor: 72.087

Review 7.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Authors:  Mana Mohan Mukherjee; Rina Ghosh; John A Hanover
Journal:  Front Mol Biosci       Date:  2022-06-14

8.  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.

Authors:  Joseph R Romeo; Luca McDermott; Clay S Bennett
Journal:  Org Lett       Date:  2020-04-13       Impact factor: 6.005

9.  Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

Authors:  Abhijit Sau; Ryan Williams; Carlos Palo-Nieto; Antonio Franconetti; Sandra Medina; M Carmen Galan
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-17       Impact factor: 15.336

10.  Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

Authors:  Carlos Palo-Nieto; Abhijit Sau; M Carmen Galan
Journal:  J Am Chem Soc       Date:  2017-09-28       Impact factor: 15.419
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