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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 …
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 …
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 …
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 …
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
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 …
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
Oxocarbenium ions are key reactive intermediates in organic chemistry. To generate a
series of structure‐reactivity‐stereoselectivity principles for these species, we herein …
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 …
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 …
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 …
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
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 …
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 …
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 …
impact on their reactivity and the stereochemical outcome of their glycosylation reactions. It …