Recent Advance in the β‐Stereoselective Synthesis of 2‐Deoxy Glycosides DOI
Qiang Zhang, Hai Dong

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(8)

Опубликована: Май 31, 2024

Abstract Compounds containing a 2‐deoxy β ‐glycoside linkage play important roles in carbohydrate chemistry, serving as potential therapies with significant biological properties. From the viewpoint of synthesis, many strategies developed recent years targeted stereoselective construction glycosides. This review aims to summarise advances synthetic routes toward β‐ glycosides over last decade. Where associated, practical applications these total synthesis natural products are highlighted.

Язык: Английский

Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates DOI Creative Commons
R. W. M. Kwok,

Ryan Rutkoski,

Pavel Nagorny

и другие.

Molecules, Год журнала: 2025, Номер 30(2), С. 218 - 218

Опубликована: Янв. 7, 2025

Using methods of DFT, we investigated the effect electron withdrawing and donating groups on relative stability tentative glycosyl donor reaction intermediates. The calculation shows that by changing stereoelectronic properties protecting group, can influence dioxolenium type intermediates up to 10 kcal mol−1, increasing nucleophillicity 4-O-Bz intermediate becomes more stable than a triflate–donor pair. We exploited this mechanism design galactosyl donors with custom O2 O4, outcome cyclohexanol. showed no change in product distribution, which suggests neighboring group participation takes precedence over remote due kinetic barriers.

Язык: Английский

Процитировано

0
Stereoselective Approaches to β-Linked 2-Deoxy Sugars DOI Creative Commons
Clay S. Bennett

Molecules, Год журнала: 2025, Номер 30(7), С. 1578 - 1578

Опубликована: Апрель 1, 2025

This review presents a survey of recent developments in the synthesis β-linked 2-deoxy sugars. Approaches ranging from catalysis to de novo are described, with focus on methods developed last 10 years. Where relevant, application these technologies and mechanistic information is discussed. Finally, it concludes an examination scope limitations technologies, as well examinations about where field should head next.

Язык: Английский

Процитировано

0
Recent Advance in the β‐Stereoselective Synthesis of 2‐Deoxy Glycosides DOI
Qiang Zhang, Hai Dong

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(8)

Опубликована: Май 31, 2024

Abstract Compounds containing a 2‐deoxy β ‐glycoside linkage play important roles in carbohydrate chemistry, serving as potential therapies with significant biological properties. From the viewpoint of synthesis, many strategies developed recent years targeted stereoselective construction glycosides. This review aims to summarise advances synthetic routes toward β‐ glycosides over last decade. Where associated, practical applications these total synthesis natural products are highlighted.

Язык: Английский

Процитировано

2