The synthesis of hyaluronic acid related oligosaccharides and elucidation of their antiangiogenic activity

Grinkova, A. A.; Сухова, Е. В.; Ustyuzhanina, Nadezhda E.; Nifantiev, Nikolay E.

doi:10.1016/j.carres.2022.108701

Cited by 3 publications

(2 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In order to prepare the hexasaccharide 3 for the introduction of the 2-acetamido-2-deoxy-β-glucose residue into acceptor 52 , a trichlorooxazoline donor 53 was chosen. Recently, the donors, which serve as precursors of trichloracetamide at C-2, have been gaining popularity because of the high yields of glycosylations , and optimized conditions for the reduction of trichloroacetamide to acetamide. , As expected, the glycosylation of pentasaccharide acceptor 52 with donor 53 was efficient and gave the hexasaccharide 54 in 80% yield.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

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

Komarova,

Novikova,

Gerbst

et al. 2023

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

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

show abstract

Section: Resultsmentioning

confidence: 99%

“…). Molecular sieves AW-300 (100.0 mg) were added to a solution of trichloroxazoline donor 5357 (22.0 mg, 0.045 mmol) and pentasaccharide acceptor 52 (87.5 mg, 0.035 mmol) in dry CH 2 Cl 2 (1.2 mL). The resulting mixture was stirred at +4 °C for 30 min.…”

mentioning

confidence: 99%