Acta Crystallographica Section C

Crystal Structure Communications

Volume 59, Part 12 (December 2003)

Acta Cryst. (2003). C59, o721-o723 [doi:10.1107/S0108270103025757]

A comparison of the ring conformational properties of two derivatives prepared from the same diene diacetate precursor

I. A. Guzei, R. W. Clark, S. D. Burke and W. T. Lambert

Abstract: 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, C₂₂H₂₆O₅, (I), and (3R,5S,6S,7S,8S)-3,6-bis(benzyloxy)-5-iodomethyl-2,3,4,5-tetrahydrofuro[3,2-b]furan-2-one, C₂₁H₂₁IO₅, (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.

Formula: C₂₂H₂₆O₅ and C₂₁H₂₁IO₅

Online 30 November 2003


	Structure factor file (CIF format) (111.2 kbytes) Contains datablock I

	Structure factor file (CIF format) (145.7 kbytes) Contains datablock II

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