256342-73-1Relevant academic research and scientific papers
Synthesis of allo - And epi -inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes
Stockton, Kieran P.,Greatrex, Ben W.,Taylor, Dennis K.
, p. 5088 - 5096 (2014/06/23)
A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.
Ruthenium carbene complexes with imidazol-2-ylidene ligands: Syntheses of conduritol derivatives reveals superior RCM activity
Ackermann, Lutz,El Tom, David,Fürstner, Alois
, p. 2195 - 2202 (2007/10/03)
Syntheses of conduritol A, E and F derivatives are described using galactitol, D-mannitol and D-glucitol, respectively, as the starting materials. The key steps of this approach comprise a Tebbe olefination reaction for the preparation of dienes 15, 21 and 27 followed by ring closing metathesis (RCM) for the formation of the polyhydroxylated cyclohexene rings of the targets. A comparative study shows that the latter transformation is best achieved with catalytic amounts of ruthenium carbene complex 3a bearing one PCy3 and one 2,3-dihydro-1H-imidazol-2-ylidene ligand in its coordination sphere. (C) 2000 Elsevier Science Ltd.
A straightforward synthesis of perbenzylated conduritols from alditols by ring closing olefin metathesis
Gallos, John K.,Koftis, Theocharis V.,Sarli, Vassiliki C.,Litinas, Konstantinos E.
, p. 3075 - 3077 (2007/10/03)
The synthesis of perbenzylated conduritols A, E and F has been achieved in six steps by formal conversion of galactitol, D-mannitol and D-glucitol into the respective terminal dienes, followed by ring closing olefin metathesis. The Royal Society of Chemistry 1999.
