TY - JOUR
T1 - DL-cyclocanaline (cyclohomoserine) and related compounds
AU - Frankel, M.
AU - Knobler, Y.
AU - Bonni, E.
AU - Bittner, S.
AU - Zvilichovsky, G.
PY - 1969
Y1 - 1969
N2 - DL-Cyclocanaline (4-aminotetrahydro-1,2-oxazin-3-one) hydrochloride, the higher homologue of the antibiotic cycloserine, has been prepared from canaline (2-amino-4-amino-oxybutyric acid) dihydrochloride. Its chemical and physical properties are reported. α-N-Triphenylmethyl- and α-N-benzoyl-cyclocanaline have been synthesised by N-tritylation of the oxa-lactam and by cyclisation of the α-benzamidocanaline ester derivative, respectively. Derivatives of DL-canaline ester bearing various protecting groups on the amino- and aminooxy-groups were obtained; N-benzyloxycarbonylhydroxylamine was utilised for the introduction of the amino-oxy group.
AB - DL-Cyclocanaline (4-aminotetrahydro-1,2-oxazin-3-one) hydrochloride, the higher homologue of the antibiotic cycloserine, has been prepared from canaline (2-amino-4-amino-oxybutyric acid) dihydrochloride. Its chemical and physical properties are reported. α-N-Triphenylmethyl- and α-N-benzoyl-cyclocanaline have been synthesised by N-tritylation of the oxa-lactam and by cyclisation of the α-benzamidocanaline ester derivative, respectively. Derivatives of DL-canaline ester bearing various protecting groups on the amino- and aminooxy-groups were obtained; N-benzyloxycarbonylhydroxylamine was utilised for the introduction of the amino-oxy group.
UR - http://www.scopus.com/inward/record.url?scp=37049117782&partnerID=8YFLogxK
U2 - 10.1039/j39690001746
DO - 10.1039/j39690001746
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AN - SCOPUS:37049117782
SN - 0022-4952
SP - 1746
EP - 1749
JO - Journal of the Chemical Society C: Organic Chemistry
JF - Journal of the Chemical Society C: Organic Chemistry
IS - 13
ER -