161754-57-0Relevant articles and documents
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.
Asymmetric synthesis using reactions with modest group selectivity
Ward, Dale E.,Liu, YaDong,Rhee, Chung K.
, p. 1429 - 1446 (2007/10/02)
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
