Mechanisms of stereodirecting participation and ester migration from near and far in glycosylation and related reactions

AA Hettikankanamalage, R Lassfolk, FS Ekholm… - Chemical …, 2020 - ACS Publications
This review is the counterpart of a 2018 Chemical Reviews article (Adero, PO; Amarasekara,
H.; Wen, P.; Bohé, L.; Crich, D. Chem. Rev. 2018, 118, 8242–8284) that examined the …

Automated chemical oligosaccharide synthesis: novel approach to traditional challenges

M Panza, SG Pistorio, KJ Stine… - Chemical reviews, 2018 - ACS Publications
Advances in carbohydrate chemistry have certainly made common oligosaccharides much
more accessible. However, many current methods still rely heavily upon specialized …

[HTML][HTML] Stereocontrolled 1, 2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry

SS Nigudkar, AV Demchenko - Chemical science, 2015 - pubs.rsc.org
Recent developments in stereoselective 1, 2-cis glycosylation that have emerged during the
past decade are surveyed herein. For detailed coverage of the previous achievements in the …

Selective prebiotic formation of RNA pyrimidine and DNA purine nucleosides

J Xu, V Chmela, NJ Green, DA Russell, MJ Janicki… - Nature, 2020 - nature.com
The nature of the first genetic polymer is the subject of major debate. Although the 'RNA
world'theory suggests that RNA was the first replicable information carrier of the prebiotic era …

Mechanisms of glycosylation reactions studied by low-temperature nuclear magnetic resonance

TG Frihed, M Bols, CM Pedersen - Chemical reviews, 2015 - ACS Publications
Synthesis of oligosaccharides has, for the past couple of decades, been greatly improved by
new methods and the ongoing development of new technologies, such as automation in …

Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of α‐Glycans up to a 30‐mer

Y Zhang, H He, Z Chen, Y Huang, G Xiang… - Angewandte …, 2021 - Wiley Online Library
The efficient synthesis of long, branched, and complex carbohydrates containing multiple 1,
2‐cis glycosidic linkages is a long‐standing challenge. Here, we report a merging reagent …

Venturing beyond donor-controlled glycosylation: new perspectives toward anomeric selectivity

WL Leng, H Yao, JX He, XW Liu - Accounts of Chemical Research, 2018 - ACS Publications
Conspectus Glycans are complex compounds consisting of sugars linked glycosidically,
existing either as pure polysaccharides or as part of glycoconjugates. They are prevalent in …

Boronic-Acid-Catalyzed Regioselective and 1,2-cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via SNi-Type Mechanism

M Tanaka, A Nakagawa, N Nishi, K Iijima… - Journal of the …, 2018 - ACS Publications
Regio-and 1, 2-cis-stereoselective chemical glycosylation of unprotected glycosyl acceptors
has been in great demand for the efficient synthesis of natural glycosides. However …

Hydrogen-bond-mediated aglycone delivery: focus on β-mannosylation

SG Pistorio, JP Yasomanee, AV Demchenko - Organic letters, 2014 - ACS Publications
O-Picoloyl groups at remote positions can mediate the course of glycosylation reactions by
providing high facial selectivity for the H-bond-mediated attack of the glycosyl acceptor. A …

[HTML][HTML] Recent Advances in Stereoselective Chemical O-Glycosylation Reactions

MM Mukherjee, R Ghosh, JA Hanover - Frontiers in Molecular …, 2022 - frontiersin.org
Carbohydrates involving glycoconjugates play a pivotal role in many life processes. Better
understanding toward glycobiological events including the structure–function relationship of …