147072-61-5Relevant academic research and scientific papers
Stereospecific synthesis of sugar-1-phosphates and their conversion to sugar nucleotides
Timmons, Shannon C.,Jakeman, David L.
, p. 865 - 874 (2008/09/16)
As Leloir glycosyltransferases are increasingly being used to prepare oligosaccharides, glycoconjugates, and glycosylated natural products, efficient access to stereopure sugar nucleotide donor substrates is required. Herein, the rapid synthesis and purification of eight sugar nucleotides is described by a facile 30 min activation of nucleoside 5′-monophosphates bearing purine and pyrimidine bases with trifluoroacetic anhydride and N-methylimidazole, followed by a 2 h coupling with stereospecifically prepared sugar-1-phosphates. Tributylammonium bicarbonate and tributylammonium acetate were the ion-pair reagents of choice for the C18 reversed-phase purification of 6-deoxysugar nucleotides, and hexose or pentose-derived sugar nucleotides, respectively.
Stereoselective synthesis of α-L-rhamnopyranosyl phosphonates via α-L-rhamnopyranosyl trifluoroacetate
Li,Li,Li
, p. 2545 - 2551 (2007/10/02)
α-L-Rhamnopyranosyl phosphates 8a-b ~ 12a-b were obtained in high yield and high stereoselectivity from α-L-rhamnopyranosyl trifluoroacetate 2a-b and phosphoric acid diesters in the presence of a Lewis acid.
Glycosyl Imidates, 37. - Direct O-Glycosylation of Compounds Containing a PO(OH) Moiety
Esswein, Angelika,Schmidt, Richard R.
, p. 675 - 678 (2007/10/02)
The O-benzylated α- and β-glucosyl trichloroacetimidates 1a-α and 1a-β afforded with the phosphinic acid derivative 2 and the phosphonic acid derivative 3 directly the corresponding O-glucosylated products 4 and 5, resp., with inversion at the anomeric ce
