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DOI: 10.1055/s-0042-1751375
A Practical and Economical Route to (S)-Glycidyl Pivalate
We thank the Bill and Melinda Gates Foundation for continuous support of our research.
Abstract
An efficient method to prepare enantiopure (S)-glycidyl pivalate from (R)-epichlorohydrin and pivalic acid is reported. This work provides an alternative to the synthesis of this important building block from readily available and inexpensive materials.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751375.
- Supporting Information
Publikationsverlauf
Eingereicht: 25. August 2022
Angenommen nach Revision: 15. September 2022
Artikel online veröffentlicht:
19. Oktober 2022
© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References and Notes
- 1a Stover CK, Warrener P, VanDevanter DR, Sherman DR, Arain TM, Langhorne MH, Anderson SW, Towell JA, Yuan Y, McMurray DN, Kreiswirth BN, Barry CE, Baker WR. Nature 2000; 405: 962
- 1b Conradie F, Diacon AH, Ngubane N, Howell P, Everitt D, Crook AM, Mendel CM, Egizi E, Moreira J, Timm J, McHugh TD, Wills GH, Bateson A, Hunt R, Niekerk CV, Li M, Olugbosi M, Spigelman M. N. Engl. J. Med. 2020; 382: 893
- 2a Orita A, Miwa K, Uehara G, Otera J. Adv. Synth. Catal. 2007; 349: 2136
- 2b Thompson AM, Blaser A, Anderson RF, Shinde SS, Franzblau SG, Ma Z, Denny WA, Palmer BD. J. Med. Chem. 2009; 52: 637
- 2c Marsini MA, Reider PJ, Sorensen EJ. J. Org. Chem. 2010; 75: 7479
- 2d Thompson AM, Sutherland HS, Palmer BD, Kmentova I, Blaser A, Franzblau SG, Wan B, Wang Y, Ma Z, Denny WA. J. Med. Chem. 2011; 54: 6563
- 2e Thompson AM, Bonnet M, Lee HH, Franzblau SG, Wan B, Wong GS, Cooper CB, Denny WA. ACS Med. Chem. Lett. 2017; 8: 1275
- 2f Chen G, Zhu M, Chen Y, Miao W, Guo M, Jiang N, Zhai X. Chem. Pap. 2020; 74: 3937
- 2g Strassfeld DA, Wickens ZK, Picazo E, Jacobsen EN. J. Am. Chem. Soc. 2020; 142: 9175
- 3 Private correspondence.
- 4 Market costs and volumes from Indian Descartes Datamyne Import/Export Data.
- 5a Phyllis E. US2537981, 1951
- 5b Mueller AC. US2772296, 1956
- 5c June RK, Rapean JC. US3075999, 1963
- 5d Kloos N, Drost JJ. J. US3178454, 1965
- 5e Smith DR. US3335156, 1967
- 5f Hosokawa H, Shikatsu M, Fujimoto T. US5380884, 1995
- 5g Rosenbrand GG, Stichter H, Heymans DM. C. US6433217, 2002
- 5h Gouman J, van der Lee SR, van’t Sand R. US8802872, 2014
- 5i Yaegashi K, Furukawa Y. US6946566, 2005
- 5j Jiang C, Ye C, Wang X, Yu Y. CN101723920, 2010
- 5k Benshun C. CN104829584, 2015
- 6 Chenyu C, Changming C, Chaoming H, Yi L, Yang L, Ling W, Ying X, Lin Z. WO2012037861, 2012
- 7 Leuschner J, Schäfer H, Leuschner F. Eur. J. Med. Chem. 1994; 29: 241
- 8 Sung JU, Seong SY, Kim YS, Park JH. US20200299247, 2020
- 9 Ciblat S, Kim J, Stewart CA, Wang J, Forgione P, Clyne D, Paquette LA. Org. Lett. 2007; 9: 719
- 10 Brachman AE, Fang JC. J. Org. Chem. 1959; 24: 1369
- 11 See the Supporting Information for details.