TY - JOUR
T1 - Synthesis of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazoles
AU - Ung, A.T.
AU - Pyne, S.G.
AU - Jeoffreys, G.R.
AU - Skelton, Brian
AU - White, Allan
PY - 2011
Y1 - 2011
N2 - The syntheses of two diastereoisomers of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazole are reported. The synthesis of these diastereoisomers involved the coupling of 5-metallated 2-(1,1-dimethoxyethyl)thiazole with a Weinreb amide derived from delta-gluconolactone, followed by asymmetric reduction of the ketone thus prepared. The stereochemistries and structures of some key compounds were determined by single-crystal X-ray structural analysis.
AB - The syntheses of two diastereoisomers of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazole are reported. The synthesis of these diastereoisomers involved the coupling of 5-metallated 2-(1,1-dimethoxyethyl)thiazole with a Weinreb amide derived from delta-gluconolactone, followed by asymmetric reduction of the ketone thus prepared. The stereochemistries and structures of some key compounds were determined by single-crystal X-ray structural analysis.
U2 - 10.1007/s00706-011-0448-z
DO - 10.1007/s00706-011-0448-z
M3 - Article
SN - 0026-9247
VL - 142
SP - 297
EP - 303
JO - MONATSHEFTE FUR CHEMIE
JF - MONATSHEFTE FUR CHEMIE
ER -