TY - JOUR
T1 - A highly stereoselective synthesis of 1-amino-2,5-anhydro-1-deoxyhexitols via 2-trifluoromethyl-oxazolinium intermediates
AU - Norrild, Jens Chr.
AU - Pedersen, Christian
AU - Søtofte, Inger
PY - 1997
Y1 - 1997
N2 - A series of 1-amino-2,5-anhydro-1-deoxyhexitols, namely derivatives of 1-amino-2,5-anhydro-1-deoxy-D-glucitol, -D-mannitol and D-talitol was prepared from the corresponding 1,3-dideoxy-1-trifluoroacetamido-D-ribo-hexitol and 1-deoxy-1-trifluoroacetamido-L-rhamnitol which both gave the expected C-2 inverted anhydrides. The reaction mechanism involves 2-trifluoromethyl-oxazolinium intermediates, which further undergo intramolecular attack of HO-5 at C-2 with inversion of the configuration. The reaction is stereospecific and highly regioselective. The crystal structure of 1-amino-2,5-anhydro-1-deoxy-D-glucitol hydrochloride is presented.
AB - A series of 1-amino-2,5-anhydro-1-deoxyhexitols, namely derivatives of 1-amino-2,5-anhydro-1-deoxy-D-glucitol, -D-mannitol and D-talitol was prepared from the corresponding 1,3-dideoxy-1-trifluoroacetamido-D-ribo-hexitol and 1-deoxy-1-trifluoroacetamido-L-rhamnitol which both gave the expected C-2 inverted anhydrides. The reaction mechanism involves 2-trifluoromethyl-oxazolinium intermediates, which further undergo intramolecular attack of HO-5 at C-2 with inversion of the configuration. The reaction is stereospecific and highly regioselective. The crystal structure of 1-amino-2,5-anhydro-1-deoxy-D-glucitol hydrochloride is presented.
U2 - 10.1016/S0008-6215(96)00278-9
DO - 10.1016/S0008-6215(96)00278-9
M3 - Journal article
SN - 0008-6215
VL - 297
SP - 261
EP - 272
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 3
ER -