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

Xian‐Xiao Chen,

Zi‐Han Li

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Дек. 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

Язык: 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

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

Himanshu Gangwar,

Anand Gaurav

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

Процитировано

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

Xinyue Xie,

Shiyin Zhao, Zhi Yang

и другие.

Chem Catalysis, Год журнала: 2024, Номер unknown, С. 101109 - 101109

Опубликована: Сен. 1, 2024

Язык: Английский

Процитировано

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

Xuan Zhang,

Xian‐Xiao Chen,

Zihan Li

и другие.

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Дек. 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

Язык: Английский

Процитировано

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

Xian‐Xiao Chen,

Zi‐Han Li

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Дек. 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

Язык: Английский

Процитировано

0