A comparison of the ring conformational properties of two derivatives prepared from the same diene diacetate precursor.
Results of single-crystal X-ray experiments performed for the title compounds, (1S,2R,3S,4R,5R)-4-benzyloxy-2-[1-(benzyloxy)allyl]-5-hydroxymethyl-2,3,4,5-tetrahydrofuran-3-ol, C(22)H(26)O(5), (I), and (3R,5S,6S,7S,8S)-3,6-bis(benzyloxy)-5-iodomethyl-2,3,4,5-tetrahydrofuro[3,2-b]furan-2-one, C(21)H(21)IO(5), (II), demonstrate that the tetrahydrofuran ring that is common to both structures adopts a different conformation in each molecule. Structural analyses of (I) and (II), which were prepared from the same precursor, indicate that their different conformations are caused by hydrogen-bonding interactions in the case of (I) and the presence of a fused bicyclic ring system in the case of (II). Density functional theory calculations on simplified analogs of (I) and (II) are also presented.
Guzei
Ilia A
IA
Chemistry Department, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706, USA. iguzei@chem.wisc.edu
Clark
Robert W
RW
Burke
Steven D
SD
Lambert
William T
WT
D000085:Acetates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D006859:Hydrogen; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D000085:Acetates; D005663:Furans; C018674:tetrahydrofuran; D006859:Hydrogen; D010100:Oxygen