148766-45-4Relevant academic research and scientific papers
Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids
Mohammed, Mohsin O.,Al Dulayymi, Juma'a R.,Baird, Mark S.
, p. 36 - 42 (2016/11/25)
An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic α-, keto and methoxy mycolic acids is described.
Arabino mycolates from synthetic mycolic acids
Mohammed, Mohsin O.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Jones, Alison,Gwenin, Christopher D.
, p. 2849 - 2857 (2016/05/19)
The synthesis of single mono-arabino mycolates, important lipid antigens from mycobacteria is described, using structurally defined synthetic mycolic acids. Preliminary assays indicate that these are differentially antigenic to antibodies in the serum of
Identification of the 5-methylthiopentosyl substituent in Mycobacterium tuberculosis lipoarabinomannan
Turnbull, W. Bruce,Shimizu, Kazumi Hiruma,Chatterjee, Delphi,Homans, Steve W.,Treumann, Achim
, p. 3918 - 3922 (2007/10/03)
An unexpected configuration of a novel carbohydrate structure in the cell wall of Mycobacterium tuberculosis was revealed by synthesizing the isomers of 5-deoxy-5-methylthio-D-pentofuranose as α- and β-methyl glycosides, and analyzing their NMR spectra (s
Enantiospecific synthesis of the phospholipase A2 inhibitor (-)-cinatrin B
Cuzzupe, Anthony N.,Di Florio, Romina,Rizzacasa, Mark A.
, p. 4392 - 4398 (2007/10/03)
The first enantiospecific synthesis of phospholipase A2 (PLA2) inhibitor (-)-cinatrin B (2) from the D-arabinose derivative 9 is described. The spirolactone system was formed by an Ireland-Claisen rearrangement of the allyl ester 8 followed by hydrolysis and stereoselective iodolactonization. The stereoselectivity of the rearrangement was controlled by the asymmetry in the allylic alcohol fragment. Ester (S)-8 gave the desired rearrangement product 7 and the epimer 13 in high yield as a 73:27 ratio, respectively. The final stereocenter at C2 was introduced via a chelation-controlled addition of the Grignard reagent derived from trimethylsilylacetylene to α-hydroxy ketone 6. Transformation of the terminal alkyne into the methyl ester 21 followed by acetal hydrolysis and selective lactol oxidation afforded cinatrin B methyl ester (22). Base hydrolysis and acid-induced relactonization then gave (-)-cinatrin B (2).
A novel route for the synthesis of deoxy fluoro sugars and nucleosides
Mikhailopulo, Igor A.,Sivets, Grigorii G.
, p. 2052 - 2065 (2007/10/03)
The reaction of (diethylamino)sulfur trifluoride (DAST) with methyl 5-O- benzoyl-β-D-xylofuranoside (1) followed by column chromatography afforded the riboside 2 (62%) and the ribo-epoxide 3 (18%) (Scheme 1). Under similar reaction conditions, the α-D-ano
