1638491-15-2Relevant academic research and scientific papers
Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis
Kang, Bubwoong,Wang, Yinli,Kuwano, Satoru,Yamaoka, Yousuke,Takasu, Kiyosei,Yamada, Ken-Ichi
supporting information, p. 4469 - 4472 (2017/04/26)
A highly site-selective N-heterocyclic carbene (NHC)-catalyzed benzoin-type cyclization of unsymmetrical dialdoses is developed to enable a divergent cyclitol synthesis. The choice of chiral NHCs and protecting groups affects the site-selectivity. The resulting inososes are converted into epi-, muco- and myo-inositols, and their chiral protected derivatives are formed in good yields.
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.
