440122-28-1Relevant academic research and scientific papers
Subtle stereochemical and electronic effects in iridium-catalyzed isomerization of C-allyl glycosides
Patnam, Ramesh,Juarez-Ruiz, Juan M.,Roy, Rene
, p. 2691 - 2694 (2007/10/03)
Stereoselective isomerization of C-allyl glycosides into (E)-C-vinyl glycosides or (2)-exo-glycals was carried out in the presence of the cationic iridium(I) catalyst [(Ph2MeP)2Ir(cod)PF6]. The products of the isomerization were affected by the relative 1,2-stereochemical relationships and by the nature of the protecting groups. These effects are discussed along with a plausible reaction mechanism.
Stereochemistry in the synthesis and reaction of exo-glycals.
Yang, Wen-Bin,Yang, Yu-Ying,Gu, Yu-Feng,Wang, Shwu-Huey,Chang, Che-Chien,Lin, Chun-Hung
, p. 3773 - 3782 (2007/10/03)
Two general methods are explored for the stereoselective synthesis of exo-glycals. One method utilizes a nucleophilic addition of fully protected sugar lactones of gluco-, galacto-, and manno-types, followed by the subsequent dehydration, to give the desired exo-glycals with (Z)-configuration. The other method proceeds with selenylation of C-glycosides in a stereoselective manner. The subsequent selenoxide elimination also provides (Z)-exo-glycals. The prepared exo-glycal conjugated esters of either gluco- or manno-type react with allyl alcohol to give exclusively alpha-anomers.
