74720-10-8Relevant academic research and scientific papers
β-Amidoaldehydes via oxazoline hydroformylation
Laitar, David S.,Kramer, John W.,Whiting, Bryan T.,Lobkovsky, Emil B.,Coates, Geoffrey W.
supporting information; experimental part, p. 5704 - 5706 (2010/01/31)
4-Substituted oxazolines, which are readily synthesized from naturally occurring α-amino acids, are converted efficiently and stereospecifically to β-amidoaldehydes in the presence of synthesis gas and catalytic dicobalt octacarbonyl.
Stereospecific synthesis of oligonucleotides containing crotonaldehyde adducts of deoxyguanosine
Nechev,Kozekov,Harris,Harris
, p. 1506 - 1512 (2007/10/03)
Crotonaldehyde reacts with DNA to form two diastereomeric 1,N2 cyclic adducts of deoxyguanosine. A synthesis of the two diastereomeric deoxynucleosides has been achieved by reaction of mixed diastereomers of 4-amino-1,2-pentanediol with 2-fluoro-O6-(trimethylsilylethyl)-deoxyinosine. The resulting N2-(1-methyl-3,4-dihydroxybutyl)-deoxyguanosine was treated with NaIO4, cleaving the vicinal diol to the aldehyde. Spontaneous cyclization gave the two diastereomers of the crotonaldehyde-adducted nucleoside that were readily separated by HPLC. The absolute configurations were assigned by an enantiospecific synthesis of one diastereomer from (S)-3-aminobutanoic acid. The synthetic strategy has been extended to preparation of a site-specifically adducted oligonucleotide by reaction of the mixed diastereomers of 4-amino-1,2-pentanediol with an 8-mer oligonucleotide containing 2-fluoro-O6-(trimethylsilylethyl)-deoxyinosine. The diastereomeric oligonucleotides were separated by HPLC and absolute configurations of the adducts were established by enzymatic digestion to the adducted nucleosides.
Selective Hydrogenation of 4,5-Dihydro-1,3-oxazin-6-ones to Carbaldehyde Derivatives; Chemical Differentiation between Acylazetidin-2-ones and the Corresponding Isomeric Oxazin-6-ones
Drey, Charles N. C.,Ridge, Richard J.,Mtetwa, Eli
, p. 378 - 380 (2007/10/02)
Catalytic hydrogenation of optically active and non-active dihydro-oxazin-6-ones unexpectedly led to preferential reduction of the carbonyl group with ring-opening yielding carbaldehyde derivatives.This reaction resolved a structural problem by leading to
