127072-92-8Relevant academic research and scientific papers
Synthesis of a mycobacterium tuberculosis tetra-acylated sulfolipid analogue and characterization of the chiral acyl chains using anisotropic NAD 2D-NMR spectroscopy
Lemetais, Aurelie,Bourdreux, Yann,Lesot, Philippe,Farjon, Jonathan,Beau, Jean-Marie
, p. 7648 - 7657 (2013/09/02)
Tetra-O-acylated sulfolipids are metabolites found in the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Their role in pathogenesis remains, however, undefined. Here we describe a novel access to model tetra-O-acylated treha
Simplified deoxypropionate acyl chains for mycobacterium tuberculosis sulfoglycolipid analogues: Chain length is essential for high antigenicity
Gau, Benjamin,Lemetais, Aurelie,Lepore, Marco,Garcia-Alles, Luis Fernando,Bourdreux, Yann,Mori, Lucia,Gilleron, Martine,De Libero, Gennaro,Puzo, Germain,Beau, Jean-Marie,Prandi, Jacques
, p. 2413 - 2417 (2014/01/06)
The longer, the better: Increasing the lengths of the 1,3-methyl-branched fatty acyl chain units in mycobacterial diacylated sulfoglycolipid (Acyl 2SGL) analogues led to dramatic improvements in their antigenic properties and gave products more
TMSOTf-catalyzed silylation: Streamlined regioselective one-pot protection and acetylation of carbohydrates
Joseph, A. Abragam,Verma, Ved Prakash,Liu, Xin-Yi,Wu, Chia-Hui,Dhurandhare, Vijay M.,Wang, Cheng-Chung
, p. 744 - 753 (2012/03/11)
A highly efficient TMSOTf-catalyzed HMDS silylation of sugars, which can easily be integrated with subsequent reactions in one-pot fashion, has been developed. Its usefulness was demonstrated by applications to streamlined regioselective one-pot protection and nonenzymatic acetylation of unprotected sugars. Monosaccharide and trehalose building blocks with orthogonally well-differentiated hydroxy groups were efficiently prepared starting with free sugars in one-pot fashion without the need for prior per-O-silylation. Regioselectively protected and acetylated building blocks were prepared directly from unprotected sugars in a one-pot manner involving up to five TMSOTf-catalyzed reactions, including a new TMSOTf-catalyzed silylation of carbohydrates. Copyright
Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides
Bourdreux, Yann,Lemetais, Aurelie,Urban, Dominique,Beau, Jean-Marie
supporting information; experimental part, p. 2146 - 2148 (2011/04/21)
Tandem catalysis by using iron(iii) chloride hexahydrate leads to carbohydrate building blocks displaying an orthogonal protecting group pattern as illustrated by the regioselective protection of trehalose and maltose disaccharides.
Synthesis of biologically potent α1 →2-linked disaccharide derivatives via regioselective one-pot protection - Glycosylation
Wang, Cheng-Chung,Lee, Jinq-Chyi,Luo, Shun-Yuan,Fan, Hsin-Fang,Pai, Chin-Ling,Yang, Wei-Chieh,Lu, Ng-Dai,Hung, Shang-Cheng
, p. 2360 - 2362 (2007/10/03)
A highly regioselective benzyl and allyl protection of D-hexopyranosides allows their application in the synthesis of biologically potent α1→2 linked disaccharide derivatives by means of a regioselective one-pot protection-glycosylation (see scheme).
Novel Disaccharide Chiral Ligands Derived from α,α-Trehalose and Their Applications to Asymmetric Hydrogenation of Enamides
Yonehara, Koji,Hashizume, Tomohiro,Ohe, Kouichi,Uemura, Sakae
, p. 1967 - 1972 (2007/10/03)
New chiral diphosphinite ligands such as 4,6 : 2′,3′ : 4′,6′-tri-O-cyclohexylidene-2,3-di-O-diphenylphosphino-α, αtrehalose (1), 3,3′-di-O-benzyl-4,6 : 4′,6′-di-O-benzylidene-2,2′-di-O-diphenylphosphino-α, α-trehalose (2), 4,6 : 4′,6′-di-O-benzylidene-2,2′-di-O-diphenylphosphino-3,3′- di-O-methyl-α,α-trehalose (3), and 2,2′-di-O-benzyl-4,6 : 4′,6′-di-O-benzylidene-3,3′-di-O-diphenylphosphino-α, α-trehalose (4) were prepared from α,α-trehalose which is an inexpensive natural reserve sugar. These ligands work as chiral ligands for Rh-catalyzed hydrogenation of α-acetamidoacrylic and cinnamic acid derivatives to afford both enantiomers of amino acids up to 84%ee (S) and 72%ee (R).
