- A straightforward synthesis of perbenzylated conduritols from alditols by ring closing olefin metathesis
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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.
- Gallos, John K.,Koftis, Theocharis V.,Sarli, Vassiliki C.,Litinas, Konstantinos E.
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- Synthesis of allo - And epi -inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes
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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.
- Stockton, Kieran P.,Greatrex, Ben W.,Taylor, Dennis K.
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p. 5088 - 5096
(2014/06/23)
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- Improved stereochemical analysis of conformationally flexible diamines by binding to a bisporphyrin molecular clip
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The relative stereochemistry of acyclic diamines with several stereogenic centers has been analyzed by NMR spectroscopy in combination with conformational deconvolution. Binding to a bisporphyrin molecular clip improves the stereochemical assignment signi
- Norrehed, Sara,Johansson, Henrik,Grennberg, Helena,Gogoll, Adolf
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supporting information
p. 14631 - 14638
(2013/11/06)
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- Separate synthesis and evaluation of glucitol bis-phosphate and mannitol bis-phosphate, as competitive inhibitors of fructose bis-phosphate aldolases
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We report the first unambiguous syntheses of glucitol-1,6-bis-phosphate and mannitol-1,6-bis-phosphate and their competitive inhibition of various fructose bis-phosphate aldolases.
- Mabiala-Bassiloua, Charles-Gabin,Zwolinska, Magdalena,Therisod, Helene,Sygusch, Jurgen,Therisod, Michel
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p. 1735 - 1737
(2008/12/21)
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- Asymmetric synthesis using reactions with modest group selectivity
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The isomeric purity of products from certain group-selective reactions can be significantly amplified when reactions can occur sequentially.The theoretical basis for a strategy that exploits reactions with modest enantiotopic group selectivity for asymmet
- Ward, Dale E.,Liu, YaDong,Rhee, Chung K.
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p. 1429 - 1446
(2007/10/02)
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