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 …

Recent advances in stereoselective glycosylation through intramolecular aglycon delivery

A Ishiwata, YJ Lee, Y Ito - Organic & biomolecular chemistry, 2010 - pubs.rsc.org
Methodology toward the stereoselective 1, 2-cis glycoside linkage using intramolecular
aglycon delivery (IAD) has been extensively developed. In the last two decades, progress …

Glycosyl-acceptor-derived borinic ester-promoted direct and β-stereoselective mannosylation with a 1, 2-anhydromannose donor

M Tanaka, J Nashida, D Takahashi, K Toshima - Organic letters, 2016 - ACS Publications
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 …

Mimicry of an HIV broadly neutralizing antibody epitope with a synthetic glycopeptide

SM Alam, B Aussedat, Y Vohra, RR Meyerhoff… - Science translational …, 2017 - science.org
A goal for an HIV-1 vaccine is to overcome virus variability by inducing broadly neutralizing
antibodies (bnAbs). One key target of bnAbs is the glycan-polypeptide at the base of the …

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

D Crich - The Journal of organic chemistry, 2011 - ACS Publications
This Perspective outlines work in the Crich group on the diastereoselective synthesis of the
so-called difficult classes of glycosidic bond: the 2-deoxy-β-glycopyranosides, the β …

Reactions of acetylenes in superbasic media. Recent advances

BA Trofimov, EY Schmidt - Russian Chemical Reviews, 2014 - iopscience.iop.org
The main advances in the chemistry of acetylene in superbasic media achieved over the last
five years are analyzed. Particular emphasis is placed on the ethynylation of aldehydes and …

Intramolecular aglycon delivery

I Cumpstey - Carbohydrate research, 2008 - Elsevier
A Minireview with 51 references covering the two-step tethering and intramolecular
glycosylation process termed intramolecular aglycon delivery (IAD). Specifically …

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

H Nguyen, D Zhu, X Li, J Zhu - Angewandte Chemie, 2016 - Wiley Online Library
A new and efficient approach for direct and stereoselective synthesis of β‐
mannopyranosides by anomeric O‐alkylation has been developed. This anomeric O …

Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

AJ Fairbanks - Beilstein journal of organic chemistry, 2018 - beilstein-journals.org
N-Glycan oxazolines have found widespread use as activated donor substrates for endo-β-
N-acetylglucosaminidase (ENGase) enzymes, an important application that has …

NAP Ether Mediated Intramolecular Aglycon Delivery: A Unified Strategy for 1,2‐cis‐Glycosylation

A Ishiwata, Y Munemura, Y Ito - 2008 - Wiley Online Library
A methodology directed towards the stereoselective construction of 1, 2‐cis‐glycosides
through naphthylmethyl (NAP) ether mediated intramolecular aglycon derivery (IAD) has …