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The configuration and conformation of di-d-fructose anhydride I. The crystal and molecular structure of 3,4,3′,4′-tetra-O- acetyl-6,6′-di(triphenylmethyl)-di-d-fructose anhydride I

✍ Scribed by M.Ashraf Shalaby; Frank R. Fronczek; Ezzat S. Younathan

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
607 KB
Volume
265
Category
Article
ISSN
0008-6215

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✦ Synopsis

The crystal structure of 3,4,3',4'-tetra-0-acetyl-6,6'-di( triphenylmethyl) -di-D-fructose anhydride I (1) has been determined by single-crystal X-ray diffraction. The crystals are monoclinic, space groupP2, witha= 16.399(2), b=9.091(2),c= 17.946(4)81, p= 103.66(l)", V=2600(2) A3, and Z= 2. The structure was refined to R=0.044 and R, = 0.051 for 4403 observed reflections. The structure analysis of 1 showed that the previously assigned chemical structure of di-D-fructose anhydride I is undoubtedly cY-D-fructofuranose /3-D-fructofuranose 1,2':2,1'-dianhydride. The conformations of the furanose rings are Es with P =59.8 and r, = 43.2" for D-fructose 1, and 'Ta with P = -34.39" and T, = 39.64" for D-fructose 2. The two furanose fragments are linked by a 1,4-dioxane ring in a Spiro arrangement. The 1,4-dioxane ring has a chair conformation with Cremer-Pople puckering parameters Q = 0.527 A, 4 = 72.2" and 8= 14.2".

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