27829-71-6Relevant articles and documents
First synthesis of 3-S-glutathionylhexanal-d8 and its bisulfite adduct
Muhl, Jennifer R.,Pilkington, Lisa I.,Deed, Rebecca C.
, (2020)
3-Sulfanylhexan-1-ol (3SH) is an impact odorant of white wines, imparting tropical fruit aromas. A reliable synthetic pathway to 3-S-glutathionylhexanal (glut-3SH-al), a precursor to 3SH that has not been intensively studied, was developed starting from 1-butanol. Application of this synthesis to 1-butanol-d10, conserved eight deuteriums, producing glut-3SH-al-d8, which can be used as an internal standard for future work on the occurrence and evolution of glut-3SH-al in wine systems. Additionally, both glut-3SH-SO3 and glut-3SH-SO3-d8 were synthesised from the corresponding aldehyde, enabling further study of the role of these bisulfite adducts in 3SH biogenesis.
N-acyl-5,5-dimethyl-oxazolidin-2-ones as latent aldehyde equivalents
Bach, Jordi,Bull, Steven D.,Davies, Stephen G.,Nicholson, Rebecca L.,Sanganee, Hitesh J.,Smith, Andrew D.
, p. 6677 - 6680 (2007/10/03)
N-acyl-5,5-dimethyl-oxazolidin-2-ones can function as versatile latent aldehyde equivalents - reductive cleavage with DIBAL-H affords aldehydes in good yield, while tandem DIBAL-H/Wittig methodology affords α,β-unsaturated esters.
THE EFFECT OF THE PHOSPHORYL SUBSTITUENTS ON THE STEREOCHEMISTRY OF THE HORNER REACTION
Larsen, Rolf Olaf,Aksnes,Gunnar
, p. 339 - 344 (2007/10/02)
The stereochemistry of the olefin forming reaction of various phosphoryl stabilized carbanions and aldehydes in ethanol is reported.The aromatic aldehydes react with acyclic phosphoryl stabilized carbanions yielding the trans isomers stereoselectively, whereas the 5- and 6-membered cyclic phosphonates (II and III) resulted in high yields of cis isomeric olefins.The aliphatic aldehydes give rise to considerable amounts of cis olefins also, decreasing in the series phosphonates, phosphinates and phosphine oxides, respectively.The stereochemical results are discussed in terms of pentacoordinated reaction intermediates.