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Short Note

[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diol

by
Margaret A. Brimble
* and
Andrew D. Johnston
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(6), M20; https://doi.org/10.3390/M20
Submission received: 18 June 1997 / Published: 20 June 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Browse Figure
Versions Notes
Molecules 02 m20 sch001 550
Scheme.
Scheme.
Molecules 02 m20 sch001
The reaction and the product ratio shown in the scheme was reported [1]. The two products (2 [1] and 3) were separated by flash chromatography using hexane-ethyl acetate (1:1) as eluent to afford the title compound 3 in the scheme) as a colourless glass (33 mg, 6%).
M.p. 63-64 deg.C.
High Res. MS calc. for C9H16O4 M+H (CI, NH3) 189.1128, found: M+ 189.1129.
IR (Nujol) cm-1 3610-3140 (br, s, OH), 1101 (s, C-O).
1H-NMR (200 MHz, CDCl3) 1.37 (1H, ddd, J11ax,11eq 12.7, J11ax, 10ax 12.7 and J11ax,10eq 4.7 Hz, 11ax-H), 1.49-1.70 (4H, m, 9-CH2 and 10-CH2), 1.85-1.98 (3H, m, 11eq-H and 4-CH2), 2.51 (2H, m, 2 x OH), 3.39 (1H, dd, J2ax,2eq 10.4 and J2ax, 3ax 10.4 Hz, 2ax-H), 3.61-3.69 (4H, m, 2eq-H, 8-CH2 and 5-H), 3.94-4.09 (1H, m, 3ax-H).
13C-NMR (50 MHz, CDCl3) 18.3, 24.9, 29.9, 35.6 (CH2, C-4, C-9, C-10 and C-11), 60.8 (CH2, C-8), 61.9 (CH, C-3), 64.3 (CH2, C-2), 71.5 (CH, C-5), 95.7 (quat, C-6).
CI-MS 189 (M+H, 8%), 171 (M+H-H2O, 100), 153 (M+H-2H2O, 15), 111 (13), 101 (6).

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgment

The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

References

  1. Brimble, M. A.; Johnston, A. D. Molecules 1997, M19.
  • Sample Availability: Available from Author, 0.1g and from MDPI, MDPI 11866.

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MDPI and ACS Style

Brimble, M.A.; Johnston, A.D. [3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diol. Molecules 1997, 2, M20. https://doi.org/10.3390/M20

AMA Style

Brimble MA, Johnston AD. [3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diol. Molecules. 1997; 2(6):M20. https://doi.org/10.3390/M20

Chicago/Turabian Style

Brimble, Margaret A., and Andrew D. Johnston. 1997. "[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diol" Molecules 2, no. 6: M20. https://doi.org/10.3390/M20

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