For Libraries For Publication Open Access Downloads About Us Contact Us
Paper Titles
Simulation Analysis of Vector Control System with Material Properties Based on Mine Fanner Load and Energy Saving
p.178
Research of High-Power Underwater Explosive Based on Analysis of Underwater Energy
p.183
Electron Beam Irradiation Degradation and Biological Treatment of 4-Chlorophenol in Aqueous Solution
p.191
Crystal Structure Characterization of 4,4-diaminodiphenyl Sulfoxide
p.195
An Improved Synthesis of 3β-Cholesteryl Halides Involving i-Steroid and Retro-i-Steroid Rearrangements
p.199
Synthesis of a Biotinylated AKT Inhibitor Analogue
p.203
A Practical Synthetic Method for Furylacryloyl-Gly-Leu-NH2
p.207
A Novel Synthesis of Glycosylated AZT-5'-Phosphoramidates
p.211
An H-Phosphonate Strategy for the Synthesis of Aciclovir 5′-triphosphate
p.215

An Improved Synthesis of 3β-Cholesteryl Halides Involving i-Steroid and Retro-i-Steroid Rearrangements

Article Preview

Abstract:

Treatment of 3β-cholesteryl methanesulfonate with tetrabutylammonium halides in the presence of BF3·Et2O provides a mild and efficient method for the preparation of 3β-cholesteryl halides via i-steroid and retro-i-steroid rearrangements. The utilization of tetrabutylammonium halides avoided the moisture sensitivity and lowered the cost of reagents for the reported method based on trimethylsilyl halides.

You might also be interested in these eBooks
Advanced Research on Energy, Chemistry and Materials Application View Preview

Info:

Periodical:

Advanced Materials Research (Volume 848)

Pages:

199-202

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.848.199

Citation:

Cite this paper

Online since:

November 2013

Authors:

Zhen Biao Xie, Shan Shan Gong, Qi Sun*

Keywords:

3β-Cholesteryl Halide, Cholesterol, Rearrangement, Steroid, Tetrabutylammonium Halide

Export:

RIS, BibTeX

Price:

Permissions CCC:

Request Permissions

Permissions PLS:

Request Permissions

Сopyright:

© 2014 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

References

[1] C. Wolfrum, S. Shi, K.N. Jayaprakash, M. Jayaraman, W. Gang, Rajendra, K.G. Rajeev, T. Nakayama, K. Charrise, E.M. Ndungo, T. Zimmermann, V. Koteliansky, M. Manoharan, M. Stoffel, Nat. Biotechnol. Vol. 25 (2007), p.1149.

DOI: 10.1038/nbt1339

Google Scholar

[2] B. Pitard, N. Oudrhiri, J.P. Vigneron, M. Hauchecorne, O. Aguerre, R. Toury, M. Airiau, R. Ramasawmy, D. Scherman, J. Crouzet, J.M. Lehn, P. Lehn, Proc. Natl. Acad. Sci. U.S.A. Vol. 26 (1999), p.2621.

DOI: 10.1073/pnas.96.6.2621

Google Scholar

[3] S.B. Sato, K. Ishii, A. Makino, K. Iwabuchi, A. Yamaji-Hasegawa, Y. Senoh, I. Nagaoka, H. Sakuraba, T. Kobayashi, J. Biol. Chem. Vol. 279 (2004), p.23790.

DOI: 10.1074/jbc.m313568200

Google Scholar

[4] R.A. Firestone, Bioconjugate Chem. Vol. 5 (1994), p.105.

Google Scholar

[5] C.C. Kan, J. Yan, R. Bittman, Biochemistry, Vol. 31 (1992), p.1866.

Google Scholar

[6] G.V. Vani, K. Vijayan, Molecular Crystals and Liquid Crystals, Vol. 51 (1979), p.253.

Google Scholar

[7] E.J. Corey, K.C. Nicolaou, M. Shibmasaki, Y. Machida, C.S. Shiner, Tetrahedron Lett. Vol. 37 (1975), p.3183.

Google Scholar

[8] R. Aneja, A.P. Davis, J.A. Knaggs, Tetrahedron Lett. Vol. 12 (1975), p.1033.

Google Scholar

[9] L. Freiberg, J. Org. Chem. Vol. 30 (1965), p.2476.

Google Scholar

[10] R.D. Haworth, L.H.C. Lunts, J. McKenna, J. Chem. Soc. (1955), p.986.

Google Scholar

[11] C.W. Shoppee, G.H.R. Summers, J. Chem. Soc. (1952), p.3361.

Google Scholar

[12] Q. Sun, S. Cai, B.R. Peterson, Org. Lett. Vol. 11(2009), p.567.

Google Scholar

© 2025 Trans Tech Publications Ltd. All rights are reserved, including those for text and data mining, AI training, and similar technologies. For open access content, terms of the Creative Commons licensing CC-BY are applied.
Scientific.Net is a registered trademark of Trans Tech Publications Ltd.