Literature DB >> 35990817

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

Ishani Lakshika Hettiarachchi1, Shuai Meng1, Mira Chahine2, Xiaohua Li2, Jianglong Zhu1.   

Abstract

A total synthesis of the trisaccharide repeat unit of Salmonella serogroup E1 O-antigen is reported. This synthesis features a key β-mannosylation reaction via cesium carbonate-mediated anomeric O-alkylation of a partially protected D-mannose with an L-fucose-derived electrophile for the first time.

Entities:  

Keywords:  Anomeric O-Alkylation; Carbohydrates; Glycosylation; Microbial Glycans; β-Mannosylation

Year:  2021        PMID： 35990817      PMCID： PMC9389860          DOI： 10.1002/ejoc.202100903

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  30 in total

1.  Formation of beta-Mannopyranosides of Primary Alcohols Using the Sulfoxide Method.

Authors:  David Crich; Sanxing Sun
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

2.  Rhamnosylation: diastereoselectivity of conformationally armed donors.

Authors:  Mads Heuckendorff; Christian Marcus Pedersen; Mikael Bols
Journal:  J Org Chem       Date:  2012-06-13       Impact factor: 4.354

3.  Rules and stereoelectronic guidelines for the anionic nucleophilic displacement of furanoside and furanose O-sulfonates.

Authors:  Karl J Hale; Leslie Hough; Soraya Manaviazar; Andrew Calabrese
Journal:  Org Lett       Date:  2015-03-17       Impact factor: 6.005

4.  Highly stereoselective β-mannopyranosylation via the 1-α-glycosyloxy-isochromenylium-4-gold(I) intermediates.

Authors:  Yugen Zhu; Biao Yu
Journal:  Chemistry       Date:  2015-04-20       Impact factor: 5.236

5.  β-Mannosylation via O-Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans.

Authors:  Shuai Meng; Bishwa Raj Bhetuwal; Hai Nguyen; Xiaotian Qi; Cheng Fang; Kevin Saybolt; Xiaohua Li; Peng Liu; Jianglong Zhu
Journal:  European J Org Chem       Date:  2020-03-19

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

Authors:  Masamichi Tanaka; Junki Nashida; Daisuke Takahashi; Kazunobu Toshima
Journal:  Org Lett       Date:  2016-04-19       Impact factor: 6.005

7.  An update of the rules for pyranoside sulfonate displacement.

Authors:  Karl J Hale; Leslie Hough; Soraya Manaviazar; Andrew Calabrese
Journal:  Org Lett       Date:  2014-09-12       Impact factor: 6.005

8.  Stereoselective Construction of β-Mannopyranosides by Anomeric O-Alkylation: Synthesis of the Trisaccharide Core of N-linked Glycans.

Authors:  Hai Nguyen; Danyang Zhu; Xiaohua Li; Jianglong Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-07       Impact factor: 15.336

Review 9.  Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research.

Authors:  Thomas J Boltje; Therese Buskas; Geert-Jan Boons
Journal:  Nat Chem       Date:  2009-11       Impact factor: 24.427

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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