Recent advances in stereoselective 1,2-cis-glycosylation DOI
Eva C. Lourenço, M. Rita Ventura

Carbohydrate chemistry, Год журнала: 2024, Номер unknown, С. 23 - 43

Опубликована: Июнь 26, 2024

1,2-cis-Glycosides have both biological and chemical significance. Their presence in natural compounds influences taste, activity drug development. Additionally, their syntheses provide avenues for research potential therapeutic applications. The construction of 1,2-cis-glycosidic bonds is still a major challenge carbohydrate synthesis. Although most organic chemists crave general methods, glycosylation reactions continue to be challenge. Since these are highly dependent on the donor–acceptor pair, solvent reagents/catalysts/promoters, one should design perfect donor fine-tune reaction conditions accordingly obtain desired stereochemical outcome. New methodologies studies reveal solutions that may not universal but can key unsolved problems. In this chapter, recent methods synthesis 1,2-cis-glycosides highlighted.

Язык: Английский

Efficient O- and S-glycosylation with ortho-2,2-dimethoxycarbonylcyclopropylbenzyl thioglycoside donors by catalytic strain-release DOI Creative Commons
Han Ding,

Jian Lv,

Xiao-Lin Zhang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(10), С. 3711 - 3720

Опубликована: Янв. 1, 2024

An efficient glycosylation reaction utilizing a meticulously designed thioglycoside has been developed. The well-established protocol was demonstrated in the total synthesis of TD139 and one-pot assembly E. coli O33 antigen tetrasaccharide.

Язык: Английский

Процитировано

10
Combination of 3-O-Levulinoyl and 6-O-Trifluorobenzoyl Groups Ensures α-Selectivity in Glucosylations: Synthesis of the Oligosaccharides Related to Aspergillus fumigatus α-(1 → 3)-d-Glucan DOI

Bozhena S. Komarova,

N.S. Novikova,

Alexey G. Gerbst

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(17), С. 12542 - 12564

Опубликована: Авг. 18, 2023

Stereospecific α-glucosylation of primary and secondary OH-group at carbohydrate acceptors is achieved using glucosyl N-phenyl-trifluoroacetimidate (PTFAI) donor protected with an electron-withdrawing 2,4,5-trifluorobenzoyl (TFB) group O-6 the participating levulinoyl (Lev) O-3. New factors have been revealed that might explain α-stereoselectivity in case TFB pentafluorobenzoyl (PFB) groups O-6. They are conformational nature confirmed by DFT calculations. The potential this donor, as well orthogonality Lev protecting groups, showcased synthesis α-(1 → 3)-linked pentaglucoside corresponding to Aspergillus fumigatus 3)-d-glucan its hexasaccharide derivative, bearing β-glucosamine residue non-reducing end.

Язык: Английский

Процитировано

7
Recent advances in stereoselective 1,2-cis-glycosylation DOI
Eva C. Lourenço, M. Rita Ventura

Carbohydrate chemistry, Год журнала: 2024, Номер unknown, С. 23 - 43

Опубликована: Июнь 26, 2024

1,2-cis-Glycosides have both biological and chemical significance. Their presence in natural compounds influences taste, activity drug development. Additionally, their syntheses provide avenues for research potential therapeutic applications. The construction of 1,2-cis-glycosidic bonds is still a major challenge carbohydrate synthesis. Although most organic chemists crave general methods, glycosylation reactions continue to be challenge. Since these are highly dependent on the donor–acceptor pair, solvent reagents/catalysts/promoters, one should design perfect donor fine-tune reaction conditions accordingly obtain desired stereochemical outcome. New methodologies studies reveal solutions that may not universal but can key unsolved problems. In this chapter, recent methods synthesis 1,2-cis-glycosides highlighted.

Язык: Английский

Процитировано

0