Australian Journal of Chemistry Australian Journal of Chemistry Society
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RESEARCH ARTICLE

Properties of Olean-12-ene-3α,16β,22α,28-tetrol and Some Derivatives

TW Hambley, TW Hambley, KG Lewis, KG Lewis, DJ Tucker, DJ Tucker, P Turner and P Turner

Australian Journal of Chemistry 49(7) 775 - 783
Published: 1996

Abstract

Reaction of olean-12-ene-3β,16β,22α,28-tetrol ( chichipegenin ) (1) with methyl orthoformate gives the 16β,22α,28-orthoformate (2). Acetylation of the ortho ester followed by hydrolysis gives the tetrol 3β-monoacetate (5). It is shown that intramolecular hydrogen bonding occurs in the tetrol (1) and the 3β-monoacetate (5) in non-polar solvents. X-Ray crystallographic data on the tetrol and its tetraacetate (4) are reported. The tetrol,C30H50O4, M 474.72, crystallized in the orthorhombic space group P 212121 with a 12.363(6), b 31.888(3), c 6.962(3) Ǻ, V 2745(1) Ǻ3, Dc(Z = 4) 1.149 g cm-3, N = N(unique) 2394, No 1878 [I > 1.5σ(I)], Nvar 500; R 0.038, Rw 0.040. The tetraacetate , C38H58O8, M 642.87, crystallized in the monoclinic space group P 21, with a 10.603(2), b 16.569(1), c 10.814(1) Ǻ, β 98.72(1)°, V 1877.9(4) Ǻ3, Dc(Z = 2) 1.137g cm-3 N 3090, Rmerge 4.67% for N(unique) 2917, No 2663 [I > 2.5σ(I)], Nvar 414; R 0.053, Rw 0.050.

https://doi.org/10.1071/CH9960775

© CSIRO 1996


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