80245-02-9Relevant academic research and scientific papers
Blurring the boundary between bio- and geohopanoids: Plakohopanoid, a C32 biohopanoid ester from Plakortis cf. lita
Costantino, Valeria,Sala, Gerardo Della,Mangoni, Alfonso,Perinu, Cristina,Teta, Roberta
, p. 5171 - 5176 (2012/10/29)
Plakohopanoid (3a), a new type of hopanoid derivative composed of a C 32 hopanoid acid ester linked to a mannosyl-myo-inositol, was isolated from the sponge Plakortis cf. lita as its peracetyl derivative 3b. The structure of 3b was determined by a combination of spectroscopic analysis and micro-scale chemical degradation. Even though plakohopanoid was isolated from a sponge, its component parts are clearly of bacterial origin, and its bacterial biosynthesis is very likely. Until now, C32 hopanoic acids have been considered to be geohopanoids, i.e., diagenetic products that are formed through abiotic degradation of the biohopanoids present in bacteria. The presence of 3a in a marine living organism shows that there is a biosynthetic pathway to C32 hopanoic acids, and these substances should therefore no longer with certainty be considered to be geohopanoids. Copyright
Methyl 1,2-orthoesters as useful glycosyl donors in glycosylation reactions: A comparison with n-pent-4-enyl 1,2-orthoesters
Uriel, Clara,Ventura, Juan,Gomez, Ana M.,Lopez, J. Cristobal,Fraser-Reid, Bert
experimental part, p. 3122 - 3131 (2012/07/13)
Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors - upon BF3·Et 2O activation in CH2Cl2 - in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective glycosylation protocols with monosaccharide diols, in which they display good regioselectivity. Copyright
Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters
Uriel, Clara,Ventura, Juan,Gomez, Ana M.,Lopez, J. Cristobal,Fraser-Reid, Bert
experimental part, p. 795 - 800 (2012/03/22)
Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.
1 Hand 13C NMR data of methyl tetra-O-benzoyl-D- pyranosides in acetone-d6
Esmurziev, Asian,Simic, Nebojsa,Sundby, Eirik,Hoff, Bard Helge
experimental part, p. 449 - 452 (2010/04/30)
Complete assignments of 1H- and 13C-NMR resonances of five methyl tetra-O-benzoyl-D-pyranosides based on 1H, 13C, 2D DQF-COSY, HMQC, HMBC and HSQC-TOCSY experiments have been performed. Copyright
Regioselective C-6 hydrolysis of methyl O-benzoyl-pyranosides catalysed by candida rugosa lipase
Esmurziev, Asian,Sundby, Eirik,Hoff, Bard Helge
body text, p. 1592 - 1597 (2009/09/08)
Hydrolysis of six methyl O-benzoyl-pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C-6, The rate of reaction was dependent on pyra
Glycolipids from sponges. Part 16.1 discoside, a rare myo-Inositol-containing glycolipid from the caribbean sponge Discodermia dissoluta
Barbieri, Lucia,Costantino, Valeria,Fattorusso, Ernesto,Mangoni, Alfonso
, p. 1527 - 1530 (2008/09/20)
Discoside (1a), a glycolipid composed of 4,6-O-diacylated mannose attached to the 2-hydroxyl group of a myo-inositol unit, was isolated as a mixture of homologues from the marine sponge Discodermia dissoluta. The complete stereostructure of this new glycolipid was solved by interpretation of mass spectrometric and NMR data and CD analysis of degradation products.
Reductive cleavage of the positional isomers of benzoylated and methylated methyl α-D-mannopyranoside
Rozanas, Christine R.,Gray, Gary R.
, p. 243 - 249 (2007/10/03)
The four O-benzoy-tri-O-methyl positional isomers, the six di-O-benzoyl-di-O-methyl positional isomers, the four tri-O-benzoyl-O-methyl positional isomers, and the tetra-O-benzoyl derivative of methyl α-D-mannopyranoside were synthesized, characterized, a
