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Short Note

2-Carbomethoxynor-31-lanosten-2-enol

1
Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, Université Cadi Ayyad, Faculté des Sciences Semlalia, BP 2390. Bd Prince My Abdellah, Marrakech. Maroc
2
LBS-UMR 6517, Centre Scientifique Saint-Jérôme, 13397 Marseille, CEDEX 20, France
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(12), M178; https://doi.org/10.3390/M178
Submission received: 29 August 2000 / Accepted: 19 October 2000 / Published: 25 December 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m178 i001
To sodium hydride (0.3g, 12.7 mmole) carefully washed with anhydrous benzene under nitrogen (to eliminate mineral oil from the commercial product) [1], was added (0.8 ml, 8.43 mmole) of dimethylcarbonate (freshly distilled) in dry benzene (20 ml). Under nitrogen atmosphere, the mixture was vigorously stirred and heated at 70 °C. At this temperature was added drop wise and during 2 hours, (1g, 2.12 mmole) of 1 [2] in dry benzene (20 ml). The agitation was maintained at 100 °C during 12 hours. After cooling to 0 °C and acidification by 5.5 ml of acetic acid, the mixture was poured on 80 ml of ice added to (80 ml) of HCl (6N). The organic layer was washed with diluted solution of sodium bicarbonate, then dried. After evaporating the solvent in vacum, the residue was purified by silica gel column chromatography using hexane as eluent to give 2 (0.85 g, 74 %).
Mp: 104-105°C.
IR: 1750 cm-1.
MS (m/z) : 471.7 (M+).
1H NMR (200 MHz, CDCl3): 12.4 (s, OH); 3.75 (s, C2'-H3); 0.75 (s, C18- H3); 0.87 (s, C19-H3); 0.95 (d, J= 6Hz, C21-H3); 0.79 (s, C28-H3); 1.22 (d, J=6Hz, C29-H3).
13C NMR (50 MHz, CDCl3):35.2 (C1); 95.9 (C2); 174.81 (C3); 39.0 (C4); 46.9 (C5); 21.6 (C6); 28.0 (C7); 135.54 (C8); 131.96 (C9); 36.2 (C10); 21.6 (C11); 25.4 (C12); 44.4 (C13); 49.7 (C14); 30.9 (C15); 30.6 (C16); 50.4 (C17); 15.7 (C18); 20.1 (C19); 36.3 (C20); 18.6 (C21); 36.3 (C22); 23.9 (C23); 39.42 (C24); 27.8 (C25); 22.9 (C26); 22.5(C27); 24.4(C28); 27.9(C29); 51.4 (C2'); 175.2 (C1').

Supplementary materials

Supplementary File 1Supplementary File 2

References

  1. Benharref, A.; Lavergne, J.-P. Bull. Soc. Chim. Fr. 1985, 965.
  2. Vander Roest, J. M.; Grieco, P. A. J. Am. Chem. Soc. 1993, 115, 5841.
  • Sample Availability: Available from the authors and MDPI.

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MDPI and ACS Style

Daoubi, M.; Benharref, A.; Pierrot, M. 2-Carbomethoxynor-31-lanosten-2-enol. Molecules 2000, 5, M178. https://doi.org/10.3390/M178

AMA Style

Daoubi M, Benharref A, Pierrot M. 2-Carbomethoxynor-31-lanosten-2-enol. Molecules. 2000; 5(12):M178. https://doi.org/10.3390/M178

Chicago/Turabian Style

Daoubi, M., A. Benharref, and M. Pierrot. 2000. "2-Carbomethoxynor-31-lanosten-2-enol" Molecules 5, no. 12: M178. https://doi.org/10.3390/M178

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