Literature DB >> 27093366

Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor.

Masamichi Tanaka1, Junki Nashida1, Daisuke Takahashi1, Kazunobu Toshima1.   

Abstract

β-Stereoselective mannosylations were conducted using a 1,2-anhydromannose donor and mono-ol acceptors in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.

Entities:  

Year:  2016        PMID： 27093366     DOI： 10.1021/acs.orglett.6b00926

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


  12 in total

1.  Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Authors:  Qiuhan Li; Samuel M Levi; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-06-26       Impact factor: 15.419

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.  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

4.  Stereoselective β-Mannosylation via Anomeric O-Alkylation with L-Sugar-Derived Electrophiles.

Authors:  Ishani Lakshika Hettiarachchi; Shuai Meng; Mira Chahine; Xiaohua Li; Jianglong Zhu
Journal:  European J Org Chem       Date:  2021-11-12

Review 5.  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

6.  Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides.

Authors:  Hidehisa Someya; Taiki Itoh; Mebae Kato; Shin Aoki
Journal:  J Vis Exp       Date:  2018-07-26       Impact factor: 1.355

7.  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

Review 8.  Intramolecular glycosylation.

Authors:  Xiao G Jia; Alexei V Demchenko
Journal:  Beilstein J Org Chem       Date:  2017-09-29       Impact factor: 2.883

9.  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.  Synthesis of Disaccharide Nucleosides Utilizing the Temporary Protection of the 2',3'-cis-Diol of Ribonucleosides by a Boronic Ester.

Authors:  Hidehisa Someya; Taiki Itoh; Shin Aoki
Journal:  Molecules       Date:  2017-10-01       Impact factor: 4.411
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