1417781-75-9Relevant academic research and scientific papers
Fragmentation of carbohydrate anomeric alkoxyl radicals: Synthesis of chiral polyhydroxylated β-iodo- and alkenylorganophosphorus(V) compounds
Hernandez-Guerra, Daniel,Rodriguez, Maria S.,Suarez, Ernesto
, p. 5033 - 5055 (2014/08/18)
A direct approach to β-iodophosphonates and β-iodophosphine oxides from 2,3-dideoxy-3-phosphoryl carbohydrate derivatives has been achieved by using the anomeric alkoxyl radical 1,2-fragmentation protocol. The reaction has been conducted on carbohydrate derivatives under mild conditions with (diacetoxyiodo)benzene and molecular iodine. Subsequent dehydroiodination afforded the corresponding vinylphosphonates and vinylphosphine oxides.
Synthesis of chiral β-iodo-and vinylorganophosphorus(V) compounds by fragmentation of carbohydrate anomeric alkoxyl radicals
Hernández-Guerra, Daniel,Rodríguez, María S.,Suárez, Ernesto
, p. 250 - 253 (2013/03/13)
A new general methodology for the synthesis of chiral vinylphosphonate and vinylphosphine oxide carbohydrate derivatives has been developed using the anomeric alkoxyl radical fragmentation reaction as the key step. The synthetic sequence proceeded via β-iodophosphonate and β-iodophosphine oxide intermediates, which may be interesting synthons for the introduction of phosphorus into organic molecules. These vinylphosphonates could be easily transformed into 2-methylene-1-phosphapentofuranoses (3-methylene-1,2- oxaphospholanes) and β-aminophosphonates, isosteres of biologically active α-methylene-γ-lactones and β-amino acids, respectively.
