ArticleThe Journal of organic chemistry2018
Interplay of Protecting Groups and Side Chain Conformation in Glycopyranosides. Modulation of the Influence of Remote Substituents on Glycosylation?
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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Who cites it
15 citing papers in PubMed, 32 citations in OpenAlex.
- Stereoselectivity of Galactosylation Reactions In Vacuo.Journal of the American Chemical Society · 2026Article
- The effect of neighbouring group participation and possible long range remote group participation inBeilstein journal of organic chemistry · 2025Review
- Synthesis of regioselectively protected building blocks of benzyl β-d-glucopyranoside.Carbohydrate research · 2024Article
- Comparison of glycosyl donors: a supramer approach.Beilstein journal of organic chemistry · 2024Article
- Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction.Science advances · 2023Article
- Stereodirecting Effect of Esters at the 4-Position of Galacto- and Glucopyranosyl Donors: Effect of 4-The Journal of organic chemistry · 2023Article
- Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides.The Journal of organic chemistry · 2022Article
- Unusual C-C bond cleavage of an α-trifloxy Sialic acid hemiacetal under Lattrell-Dax conditions.Carbohydrate research · 2022Article
- Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion byAngewandte Chemie (International ed. in English) · 2021Article
- O-Methylation in Carbohydrates: An NMR and MD Simulation Study with Application to Methylcellulose.The journal of physical chemistry. B · 2021Article
- Influence of Configuration at the 4- and 6-Positions on the Conformation and Anomeric Reactivity and Selectivity of 7-Deoxyheptopyranosyl Donors: Discovery of a Highly Equatorially Selective l-The Journal of organic chemistry · 2021Article
- Influence of substitution at the 5α-Position on the side chain conformation of glucopyranosides.Carbohydrate research · 2021Article
- Predictive Analysis of the Side Chain Conformation of the Higher Carbon Sugars: Application to the Preorganization of the Aminoglycoside Ring 1 Side Chain for Binding to the Bacterial Ribosomal Decoding A Site.The Journal of organic chemistry · 2020Article
- Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.Chemical reviews · 2020Article
- Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.Journal of the American Chemical Society · 2018Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis and conformational analysis of a series of phenyl 2,3,6-tri- O-benzyl-β-d-thio galacto- and glucopyranosides and their 6 S-deuterio isotopomers, with systematic variation of the protecting group at the 4-position, are described. For the galactopyranosides, replacement of a 4- O-benzyl ether by a 4- O-alkanoyl or aroyl ester results in a small but measurable shift in side chain population away from the trans, gauche conformation and in favor of the gauche, trans conformer. In the glucopyranoside series on the other hand, replacement of a 4- O-benzyl ether by a 4- O-alkanoyl or aroyl ester results in a small but measurable increase in the population of the trans, gauche conformer at the expense of the gauche, gauche conformer. The possible modulating effect of these conformational changes on the well-known changes in the anomeric reactivity of glycosyl donors as a function of protecting group is discussed, raising the possibility that larger changes may be observed at the transition state for glycosylation. A comparable study with a series of ethyl 2,3,4-tri- O-benzyl-β-d-thioglucopyranosides reveals that no significant influence in side chain population is observed on changing the O6 protecting group.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.