221909-84-8Relevant academic research and scientific papers
The α-Glycosidation of Partially Unprotected N-Acetyl and N-Glycolyl Sialyl Donors in the Absence of a Nitrile Solvent Effect
Aoyagi, Taku,Ohira, Shuichi,Fuse, Shinichiro,Uzawa, Jun,Yamaguchi, Yoshiki,Tanaka, Hiroshi
supporting information, p. 6968 - 6973 (2016/05/11)
The synthesis of α-sialosides is one of the most difficult reactions in carbohydrate chemistry and is considered to be both a thermodynamically and kinetically disfavored process. The use of acetonitrile as a solvent is an effective solution for the α-sel
O-sialylation with N-acetyl-5-N,4-O-carbonyl-protected thiosialoside donors in dichloromethane: Facile and selective cleavage of the oxazolidinone ring
Crich, David,Li, Wenju
, p. 2387 - 2391 (2007/10/03)
An N-acetyl-5-N,4-O-carbonyl-protected thiosialoside donor, the structure of which has been defined through X-ray crystallography, was prepared and tested in couplings to a wide range of acceptors. This donor gives excellent yields and α-selectivities in
Synthesis of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified at the C-4 and C-9 positions and their behaviour towards sialidase from influenza virus and pig liver membrane
Ikeda, Kiyoshi,Sano, Kimihiko,Ito, Masaki,Saito, Megumi,Hidari, Kazuya,Suzuki, Takashi,Suzuki, Yasuo,Tanaka, Kiyoshi
, p. 31 - 41 (2007/10/03)
The synthesis of novel 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues structurally varied at C-4 and C-9 by transformation from versatile key intermediates and their inhibitory activity against sialidase from influenza virus A and pig liver membrane are described.
Total synthesis of VIM-2 ganglioside isolated from human chronic myelogenous leukemia cells
Ehara, Taro,Kameyama, Akihiko,Yamada, Yutaka,Ishida, Hideharu,Kiso, Makoto,Hasegawa, Akira
, p. 237 - 252 (2007/10/03)
A total synthesis of the tumor-associated glycolipid antigen, VIM-2. is described. Phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1 → 4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (7), a key intermediate prepared by condensation of phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (6) and 2,3,4-tri-O-benzoyl-6-O-benzyl-α-D-galactopyranosyl bromide (5), was glycosylated with methyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (8) to give the trisaccharide donor 9, which, on coupling with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1 → 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (10), afforded the pentasaccharide 11. The regioselective glycosylation of 12 (derived by O-debenzoylation of 11) with 7 gave the heptasaccharide 13, which was converted by treatment with hydrazine monohydrate and subsequent N-acetylation into the hexasaccharide acceptor 14. The stereo- and regio-selective glycosylation of 14 with methyl (phenyl 5-acetamido-4,7,8,9-O-benzoyl-3,5-dideoxy-2-thio-D-glycero-β-D-galact o-2-nonulopyranosid)onate (16) gave the desired octasaccharide 18. Hydrogenolytic removal of the benzyl groups in 18 and successive O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile gave the α-trichloroacetimidate 21, which was then coupled with (2S,3R,4E)-2-azido-3-O-(tert-butyldiphenylsilyl)4-octadecene-1,3-diol (22) to give 23. Compound 23 was transformed, via selective reduction of the azido group, N-introduction of octadecanoic acid, O-desilylation, O-deacylation, and saponification of the methyl ester group, into the title VIM-2 ganglioside 26.
