Stereoselective P(III)‐Glycosylation for the Preparation of Phosphinated Sugars DOI
Xuan Zhang,

Xian‐Xiao Chen,

Zi‐Han Li

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

Abstract Most of the reported work focus on development O ‐, N C ‐ and S ‐glycosylation methods. However, no study explores P(III)‐glycosylation reaction. Herein we describe a convenient protocol to realize process. A simple β ‐phosphino ester is adopted as P(III)‐transfer reagent for this new type glycosylation via nucleophilic substitution release strategy. Diverse phosphine units are introduced anomeric center various sugars efficiently with excellent stereoselectivity. The value method showcased by prepared P(III)‐sugars novel linkers in bioactive molecule conjugation, chiral ligands metal‐catalyzed asymmetric allylic substitutions organocatalysts. Preliminary mechanistic studies corroborated designed

Language: Английский

Halonium and Chalconium Salt-Catalyzed Schiff Condensation: Kinetics and DFT Insights into Organocatalyst Activity Parameters DOI
Alexandra A. Sysoeva, Yana V. Safinskaya, Mikhail V. Il’in

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Chalconium and halonium salts catalyze Schiff condensation. Kinetic data DFT calculations show that the catalytic activity correlates with maximum electrostatic potential on σ-holes, whereas other factors are less significant.

Language: Английский

Citations

0
Hydrogen-Bond-Mediated Glycosylation Reactions with Glycosyl Picolinates DOI
Mohan Lal,

Himanshu Gangwar,

Anand Gaurav

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 11, 2025

Herein, we report a generally applicable hydrogen-bond-mediated glycosylation protocol of glycosyl picolinate donors with charged (thio)urea hydrogen-bond-donor catalyst. A variety nucleophiles, including complex natural products, glycosides, amino acids, and less nucleophilic phenolic acceptors were also glycosylated successfully. Hydrogen-bond-mediated systems combined different strategies explored to achieve stereoselective glycosylation. mechanistic study revealed that catalysts form the donor-catalyst noncovalent through hydrogen bonds then produce oxocarbenium species.

Language: Английский

Citations

0
Strain-Release Glycosylation of Thio- and Selenoglycosides Enabled by Activation of Donor–Acceptor Oxiranes with Catalytic TfOH DOI

Xin-Yu Fang,

Liu Xingle,

Jiaying Shen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

We have developed a strain-release glycosylation method for thio/selenoglycosides utilizing donor-acceptor oxiranes (DAOs) and triflic acid (2 mol %) via C-C bond cleavage under ambient conditions. This protocol is effective acid-sensitive sterically hindered substrates, demonstrating broad applicability. Experimental results DFT calculations reveal that DAO/TfOH-derived zwitterionic oxocarbenium species activate donors glycosyl zwitterion intermediates, facilitating glycosidic formation proton transfer. approach pioneers epoxide-mediated activation, offering mild, efficient platform diverse glycoside synthesis advancing methodologies in carbohydrate chemistry.

Language: Английский

Citations

0
Direct construction of aryl amide N-glycosides from glycosyl oxamic acids via photoredox palladium-catalyzed aminocarbonylations DOI

Xinyue Xie,

Shiyin Zhao, Zhi Yang

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 101109 - 101109

Published: Sept. 1, 2024

Language: Английский

Citations

3
Stereoselective P(III)‐Glycosylation for the Preparation of Phosphinated Sugars DOI Open Access

Xuan Zhang,

Xian‐Xiao Chen,

Zihan Li

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

Abstract Most of the reported work focus on development O ‐, N C ‐ and S ‐glycosylation methods. However, no study explores P(III)‐glycosylation reaction. Herein we describe a convenient protocol to realize process. A simple β ‐phosphino ester is adopted as P(III)‐transfer reagent for this new type glycosylation via nucleophilic substitution release strategy. Diverse phosphine units are introduced anomeric center various sugars efficiently with excellent stereoselectivity. The value method showcased by prepared P(III)‐sugars novel linkers in bioactive molecule conjugation, chiral ligands metal‐catalyzed asymmetric allylic substitutions organocatalysts. Preliminary mechanistic studies corroborated designed

Language: Английский

Citations

0
Stereoselective P(III)‐Glycosylation for the Preparation of Phosphinated Sugars DOI
Xuan Zhang,

Xian‐Xiao Chen,

Zi‐Han Li

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

Abstract Most of the reported work focus on development O ‐, N C ‐ and S ‐glycosylation methods. However, no study explores P(III)‐glycosylation reaction. Herein we describe a convenient protocol to realize process. A simple β ‐phosphino ester is adopted as P(III)‐transfer reagent for this new type glycosylation via nucleophilic substitution release strategy. Diverse phosphine units are introduced anomeric center various sugars efficiently with excellent stereoselectivity. The value method showcased by prepared P(III)‐sugars novel linkers in bioactive molecule conjugation, chiral ligands metal‐catalyzed asymmetric allylic substitutions organocatalysts. Preliminary mechanistic studies corroborated designed

Language: Английский

Citations

0