136758-36-6Relevant articles and documents
Highly stereoselective syn-hydroxylation of spiroketals
Brimble,Nairn,Wu
, p. 4049 - 4050 (1991)
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Crystal structures of (3S*,4S*,5S*,6S*)-3,4-epoxy-1,7-dioxaspiro[5.5]undecan- 5-ol, (3R*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-3,5-diyl diacetate and (4S*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-4,5-diol
Brimble, Margaret A.,Johnston, Andrew,Hambley, Trevor W.,Turner, Peter
, p. 123 - 127 (2007/10/03)
The structures of (3S*,4S*,5S*,6S*)-3,4-epoxy-1,7-dioxaspiro[5.5]undecan- 5-ol (2), (3R*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-3,5-diyl diacetate (4) and (4S*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-4,5-diol (5) have been determined by X-ray crystallography. The unsubstituted tetrahydropyran ring in (2) adopts an axial position with respect to the epoxy-substituted ring and the hydroxy group at C 5 is syn to the epoxide group. Intermolecular hydrogen bonding is observed between the C 5 hydroxy group and O1. The two six-membered rings in (4) adopt chair conformations and the two acetate groups adopt 1,3-diaxial positions. The C 5 hydroxy group in (5) assumes an axial position anti to the C-O bond of the neighbouring ring whilst 4-OH occupies an equatorial position. Intermolecular hydrogen bonding is also observed between 4-OH and 5-OH. Compound (2), C9H14O4, M 186.21, crystallized in the monoclinic space group P21/c with a 7.867(1), b 12.2060(9), c 9.3676(8) A, β 102.744(8)°, V 877.4(1) A3 and No 1163 [I > 2.5σ(I)], R 0.031, Rw 0.035. Compound (4), C13H20O6, M 272.30, crystallized in the triclinic space group P1 with a 9.902(1), b 11.0024(9), c 6.9183(5) A, α 104.078(8), β 96.769(9), γ 101.980(8)°, V 703.8(1) A3, No 1657 [I > 2.5σ(I)], R 0.047, Rw 0.044. Compound (5), C9H16O4, M 188.22, crystallized in the orthorhombic space group Pbca with a 25.504(3), b 8.909(2), c 8.038(2) A, V 1826.4(5) A3, No 1096 [I > 2.5σ(I)], R 0.030, Rw 0.030.