196298-41-6Relevant academic research and scientific papers
N-heterocyclic carbene-catalyzed benzoin strategy for divergent synthesis of cyclitol derivatives from alditols
Kang, Bubwoong,Sutou, Toshiaki,Wang, Yinli,Kuwano, Satoru,Yamaoka, Yousuke,Takasu, Kiyosei,Yamada, Ken-Ichi
, p. 131 - 147 (2015)
A divergent synthesis of cyclitol derivatives has been developed utilizing an N-heterocyclic carbene-catalyzed benzoin-type cyclization of C2-symmetrical dialdoses. The resulting inososes are versatile intermediates, which are readily converted
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.
Synthesis of cyclitols fused with a furoxan ring from alditols by intramolecular nitrile oxide dimerization
Gallos, John K.,Koftis, Theoharis V.,Karamitrou, Vassiliki I.,Koumbis, Alexandros E.
, p. 2461 - 2462 (2007/10/03)
The synthesis of cyclitols fused with a furoxan ring has been achieved by conversion of an alditol to a bis-(aldoxime) and further oxidation of the oxime groups with N-chlorosuccinimide to nitrile oxides, which spontaneously dimerize intramolecularly to form a furoxan ring.
