The X-ray crystal structure of 2,3:4,5-di-O-isopropylidene-1-O-methyl-beta-D-fructopyranose

Carbohydr Res. 1990 Mar 25:197:33-40. doi: 10.1016/0008-6215(90)84127-g.

Abstract

2,3:4,5-Di-O-isopropylidene-1-O-methyl-beta-D-fructopyranose, C13H22O6, Mr = 274.3, orthorhombic, P212121, a = 12.388 (2), b = 13.307 (5), c = 8.660 (1) A, V = 1427.4 (9) A3, Z = 4, Dm = 1.24 g.cm-3, Dx = 1.276 g.cm-3, CuKalpha, lambda = 1.54184 A, mu = 8.0 cm-1, F(000) = 592, T = 295 (1) K, R = 0.032 for 1586 observations (of 1693 unique data). The molecule is a derivative of the naturally occurring carbohydrate D-fructose. The data reported here indicate that the ketose six-membered ring is constrained by the presence of two fused five-membered rings into the 3SO conformation. These findings agree with the n.m.r.-spectroscopic results for 2,3:4,5-di-O-benzylidene-beta-D-fructopyranose. As a result of crystal packing forces, the exocyclic side-chain has a C-C-O-C torsion angle of -102 degrees, quite different from the expected value of 180 degrees.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbohydrate Conformation
  • Fructose / analogs & derivatives*
  • Fructose / analysis
  • X-Ray Diffraction

Substances

  • Fructose
  • 2,3-4,5-di-O-isopropylidene-1-O-methyl-beta-fructopyranose