115093-65-7Relevant academic research and scientific papers
One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides
Dash, Ashutosh K.,Madhubabu, Tatina,Yousuf, Syed Khalid,Raina, Sushil,Mukherjee, Debaraj
, p. 1 - 8 (2016/12/22)
One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high α-selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides.
Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement
Chen, Peiran,Su, Jie
supporting information, p. 84 - 94 (2015/12/23)
By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.
Selective Deoxygenation of Unsaturated Carbohydrates with Pd(0)/Ph2SiH2/ZnCl2. Total Synthesis of (+)-(S,S)-(6-Methyltetrahydropyran-2-yl)acetic Acid
Greenspoon, Noam,Keinan, Ehud
, p. 3723 - 3731 (2007/10/02)
Highly chemoselective reductive cleavage of allylic acetates of 1,2- and 2,3-unsaturated monosaccharides was achieved by a three-component reducing system comprised of diphenylsilane, a soluble palladium(0) catalyst, and catalytic amounts of zinc chloride.It was demonstrated that hydride substitution proceeds with absolute inversion of configuration at the carbon, implying that hydride is initially transferred to palladium and from there to the allylic ligand.The usefulness of the new chiral building blocks thus formed was demonstrated by the total synthesis of the civet constituent, (+)-(2S,6S)-cis-(6-methyltetrahydropyran-2-yl)acetic acid and its 2R,6S-trans isomer.
