Literature DB >> 20585666

Recent advances in stereoselective glycosylation through intramolecular aglycon delivery.

Akihiro Ishiwata1, Yong Joo Lee, Yukishige Ito.   

Abstract

Methodology toward the stereoselective 1,2-cis glycoside linkage using intramolecular aglycon delivery (IAD) has been extensively developed. In the last two decades, progress has been made using various mixed acetal linkages and a number of glycosyl donor moieties to develop novel IAD strategies, mainly based on formation of acetal linkages. This account summarizes the newest naphthylmethyl (NAP) ether-mediated IAD as well as all the types of mediations for stereospecific construction of various 1,2-cis linkages, not only for beta-mannopyranoside, but also for other linkages almost without exception, including beta-L-rhamnoside.

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Year:  2010        PMID: 20585666     DOI: 10.1039/c004281a

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


  20 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.  Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors:  Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal:  Chem Rev       Date:  2020-07-05       Impact factor: 60.622

3.  Selective prebiotic formation of RNA pyrimidine and DNA purine nucleosides.

Authors:  Jianfeng Xu; Václav Chmela; Nicholas J Green; David A Russell; Mikołaj J Janicki; Robert W Góra; Rafał Szabla; Andrew D Bond; John D Sutherland
Journal:  Nature       Date:  2020-06-03       Impact factor: 49.962

4.  Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects.

Authors:  Xiao G Jia; Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  J Org Chem       Date:  2016-12-07       Impact factor: 4.354

5.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

6.  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

7.  Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors.

Authors:  Philip O Adero; Takayuki Furukawa; Min Huang; Debaraj Mukherjee; Pascal Retailleau; Luis Bohé; David Crich
Journal:  J Am Chem Soc       Date:  2015-08-07       Impact factor: 15.419

8.  Stereoselective Synthesis of 2-Azido-2-deoxy-β-d-mannosides via Cs2CO3-Mediated Anomeric O-Alkylation with Primary Triflates: Synthesis of a Tetrasaccharide Fragment of Micrococcus luteus Teichuronic Acid.

Authors:  Bishwa Raj Bhetuwal; Fenglang Wu; Shuai Meng; Jianglong Zhu
Journal:  J Org Chem       Date:  2020-11-17       Impact factor: 4.354

9.  Cation clock permits distinction between the mechanisms of α- and β-O- and β-C-glycosylation in the mannopyranose series: evidence for the existence of a mannopyranosyl oxocarbenium ion.

Authors:  Min Huang; Pascal Retailleau; Luis Bohé; David Crich
Journal:  J Am Chem Soc       Date:  2012-08-31       Impact factor: 15.419

10.  Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation.

Authors:  Papapida Pornsuriyasak; Xiao G Jia; Sophon Kaeothip; Alexei V Demchenko
Journal:  Org Lett       Date:  2016-04-26       Impact factor: 6.005

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