TY - JOUR
T1 - Conformational studies of 3'-C-methyl and 2'-C-methyl analogs of cordycepin
AU - Koole, L.H.
AU - Buck, H.M.
AU - Bazin, H.
AU - Chattopadhyaya, J.
PY - 1987
Y1 - 1987
N2 - A high resolution 1H NMR conformational analysis study of a 3'- -methyl (compound (1)) and a 2'- -methyl (compound (2)) analogue of cordycepin, a naturally occurring anitibiotic, has been performed. For compound (1) it is found that the methyl group on C3, leads to an entirely different molecular conformation, which is determined primarily by a strong intramolecular hydrogen bond between O5, and N3 of the syn-oriented adenine base. This particular conformation results in very unusual broadening of the H5' resonances in the case of CDCl3 as solvent. Furthermore, the synthesis of compound (2) via a regiospecific Grignard-type reaction is described. Conformational analysis of compound (2) revealed that the methyl group on C2, shifts the conformational equilibrium of the furanose ring towards South.
AB - A high resolution 1H NMR conformational analysis study of a 3'- -methyl (compound (1)) and a 2'- -methyl (compound (2)) analogue of cordycepin, a naturally occurring anitibiotic, has been performed. For compound (1) it is found that the methyl group on C3, leads to an entirely different molecular conformation, which is determined primarily by a strong intramolecular hydrogen bond between O5, and N3 of the syn-oriented adenine base. This particular conformation results in very unusual broadening of the H5' resonances in the case of CDCl3 as solvent. Furthermore, the synthesis of compound (2) via a regiospecific Grignard-type reaction is described. Conformational analysis of compound (2) revealed that the methyl group on C2, shifts the conformational equilibrium of the furanose ring towards South.
U2 - 10.1016/S0040-4020(01)86838-1
DO - 10.1016/S0040-4020(01)86838-1
M3 - Article
SN - 0040-4020
VL - 43
SP - 2989
EP - 2997
JO - Tetrahedron
JF - Tetrahedron
IS - 13
ER -