590367-95-6Relevant academic research and scientific papers
Synthesis of α-O- and α-S-glycosphingolipids related to sphingomonous cell wall antigens using anomerisation
Pilgrim, Wayne,O'Reilly, Ciaran,Murphy, Paul V.
, p. 11198 - 11218 (2013/10/22)
Analogues of glycolipids from Spingomonadacaece with O- and S- and SO 2-linkages have been prepared using chelation induced anomerisation promoted by TiCl4. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as well as isomerisation of β-thioglycuronic acids (β-glycosyl thiols). The β-O-glucuronide and β-O-galacturonide precursors were efficiently prepared using benzoylated trichloroacetimidates. β-Glycosyl thiols were precursors to β-S-derivatives. Triazole containing mimics of the natural glycolipids were prepared using CuI promoted azide-alkyne cycloaddition reactions in THF. The glycolipid antigens are being evaluated currently for their effects on iNKT cells.
Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase
Guo, Tiantian,Liu, Qingchao,Wang, Peng,Zhang, Lei,Zhang, Wei,Li, Yingxia
body text, p. 1167 - 1174 (2009/10/04)
The first synthesis of scabiosaponins E (1), F (2), and G (3), three new oleanolic acid saponins with strong inhibitory activity on pancreatic lipase isolated from the Chinese traditional medicinal herb Scabiosa tschiliensis, was efficiently achieved in an one-pot strategy under the combined use of glycosyl trichloroacetimidates and p-toluene 1-thioglycosides (STol) as donors.
α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives
Pilgrim, Wayne,Murphy, Paul V.
supporting information; experimental part, p. 939 - 942 (2009/09/08)
Bacterial glycolipids containing either α-glucuronic acid or α-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel α-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.
Synthesis of a new phenol glycoside, neohancoside C from Cynanchum hancockianum
Konda, Yaeko,Iwasaki, Yayoi,Takahata, Shihomi,Arima, Shiho,Toida, Tsuneyuki,Kaji, Eisuke,Takeda, Kazuyoshi,Harigaya, Yoshihiro
, p. 626 - 630 (2007/10/03)
Neohancoside C (1) is a new phenol glycoside isolated from Cynanchum hancockianum, which is a Chinese folk medicine having antitumor activity. The synthesis of 1, 2-acetylphenyl β-D-xylopyranosyl-(1→6)-β-D-gluco- pyranoside, was achieved by phase-transfer
