Stereochemical Aspects of the C-Glycosylation of Pyranosides and Furanosides

S Achanta, CVA Sasikala, D Basu, PD Nahide… - …, 2024 - thieme-connect.com
The stereoselective synthesis of α-and β-C-glycosides is one of the most challenging areas
of research in the field of glycoside chemistry. In this review, we summarize the various …

Anomeric triflates versus dioxanium ions: Different product-forming intermediates from 3-acyl benzylidene mannosyl and glucosyl donors

WA Remmerswaal, H Elferink… - The Journal of …, 2024 - ACS Publications
Minimal structural differences in the structure of glycosyl donors can have a tremendous
impact on their reactivity and the stereochemical outcome of their glycosylation reactions …

Neighboring‐Group Participation by C‐2 Acyloxy Groups: Influence of the Nucleophile and Acyl Group on the Stereochemical Outcome of Acetal Substitution …

Y Chun, WA Remmerswaal, JDC Codée… - … A European Journal, 2023 - Wiley Online Library
A single acyloxy group at C‐2 can control the outcome of nucleophilic substitution reactions
of pyran‐derived acetals, but the extent of the neighboring‐group participation depends on a …

Acetal Substitution Reactions: Stereoelectronic Effects, Conformational Analysis, Reactivity vs Selectivity, and Neighboring-Group Participation

Y Chun, KB Luu, KA Woerpel - Synlett, 2024 - thieme-connect.com
Acetal substitution reactions can proceed by a number of mechanisms, but oxocarbenium
ion intermediates are involved in many of these reactions. Our research has focused on …

Origin of Stereoselectivity in SE2′ Reactions of Six‐membered Ring Oxocarbenium Ions

WA Remmerswaal, T Hansen… - … A European Journal, 2023 - Wiley Online Library
Oxocarbenium ions are key reactive intermediates in organic chemistry. To generate a
series of structure‐reactivity‐stereoselectivity principles for these species, we herein …

Stereoselective access to 2-deoxy-2-trifluoromethyl sugar mimetics by trifluoromethyl-directed 1, 2-trans glycosylation

J Mestre, I Bascuas, M Bernús, S Castillón… - Organic Chemistry …, 2023 - pubs.rsc.org
Fluorinated carbohydrate mimetics are valuable molecular fragments in contemporary
Glycoscience. Available synthetic protocols are mainly restricted to the preparation of …

Neighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2-trans Stereoselectivity in Nucleophilic Substitution …

Y Chun, WA Remmerswaal, JDC Codée… - The Journal of …, 2025 - ACS Publications
Nucleophilic substitution reactions of C-2-acyloxy furanosyl acetals can be highly
diastereoselective. We here show that the presence of a less electron-donating p …

The influence of acceptor acidity on hydrogen bond mediated aglycone delivery (HAD) through the picoloyl protecting group

WA Remmerswaal, D Hoogers… - European Journal of …, 2024 - Wiley Online Library
The outcome of glycosylation reactions heavily relies on the specific protecting group
patterns employed on both the donor and acceptor molecules. The picoloyl (Pico) protecting …

Application of BF3• OEt2 in Organic Synthesis as a Catalyst or Synthon

C Zujia, Y Shiwei, Z Yongjun, L Huanqing… - Chinese Journal of …, 2023 - sioc-journal.cn
BF 3• OEt 2, as a typical Lewis acid catalyst with excellent catalytic capacity, plays an
important role in many reactions, such as coupling, cyclization and rearrangement, and it is …

Anomeric Triflates vs Dioxanium ions: Different Product-Forming Intermediates from 1-Thiophenyl-2-O-Benzyl-3-O-Benzoyl-4, 6-O-Benzylidene-Mannose and Glucose

W Remmerswaal, H Elferink, K Houthuijs, T Hansen… - 2023 - chemrxiv.org
Minimal structural differences in the structure of glycosyl donors can have a tremendous
impact on their reactivity and the stereochemical outcome of their glycosylation reactions. It …