204187-64-4Relevant academic research and scientific papers
Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000
Chaulagain, Mani Raj,Postema, Maarten H.D.,Valeriote, Fred,Pietraszkewicz, Halina
, p. 7791 - 7794 (2007/10/03)
A ring-closing metathesis approach was employed for the synthesis of a β-C-glycoside analog of the immunostimulant KRN7000. The protected C-glycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit
Expeditious synthesis of β-linked glycosyl serine methylene isosteres (β-C-Gly Ser) via ethynylation of sugar lactones
Dondoni,Mariotti,Marra,Massi
, p. 2129 - 2137 (2007/10/03)
The addition of the lithium derivative of N-Boc 4-ethynyl-2,2-dimethyl-1,3-oxazolidine to tetra-O-benzyl-D-gluco- and galactonolactone and 2-azido-2-deoxy congeners afforded the corresponding ethynyl ketoses in fairly good yields (64-78%). Following the conversion of the ketoses into O-acetates and removal of the acetoxy group by silane reduction, the resulting β-linked ethynyl glycosides were transformed into N-Boc C-glycosyl α-aminobutyric acids by reduction of the triple bond using H2/Pd(OH)2 and oxidative cleavage of the oxazolidine ring using the Jones' reagent. After the removal of O-benzyl groups of the carbohydrate moieties by hydrogenation and the reduction of azido to amino group, all compounds were subjected to acetylation and isolated as O- and N-acetyl derivatives. The C-glycosyl α-amino acids prepared correspond to methylene isosteres of O-glycosyl serines.
Design and use of an oxazolidine silyl enol ether as a new homoalanine carbanion equivalent for the synthesis of carbon-linked isosteres of O- glycosyl serine and N-glycosyl asparagine
Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
, p. 933 - 944 (2007/10/03)
A trimethylsilyl enol ether carrying the N-Boc 2,2-dimethyloxazolidine ring was designed to serve as a synthetic equivalent of the homoalanine carbanion for the introduction of the α-amino acid side chain at the anomeric carbon of sugars. This new functio
Synthesis of methylene isosteres of α- And β-D-galactopyranosyl-L-serine
Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
, p. 1741 - 1742 (2007/10/03)
The BF3·Et2O promoted coupling of tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate with a silyl enol ether carrying an oxazolidine ring leads to the α-C-glycosylmethyl ketone (32%, 95% ds) that is converted into the title α-C
Stereoselective synthesis of the C-linked analogue of β-D-galactopyranosyl-L-serine
Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
, p. 2827 - 2832 (2007/10/03)
The coupling of the D-serinal derivative 7 with the D-galactopyranosylmethylene phosphorane generated from the phosphonium salt 6 and reduction of the resulting alkene led to the C-glycosylated amino alcohol 9 that in turn was oxidized to the title amino acid in 44% overall yield.
