Selective Deprotection of Strategy for TBS Ether Under Mild Condition
Vol 2, Issue 1, 2019
VIEWS - 1235 (Abstract) 277 (PDF)
Abstract
A selective, high yielding and convenient method for deprotection of tert-butyldimethylsilyl ether (TBS) using catalytic amount of ZnBr2and N-chlorosuccinimide in methanol/DCM as solvent at room temperature is described. The methodology iseconomical, robust, clean, rapid, high yielding and highly selective in for deprotection of TBS ether.Methodology is applicable for deprotection of acetonide also.
Keywords
Full Text:
PDFReferences
1. Greene TW, Wuts PGM. Protective Groups in OrganicSynthesis. 3rd ed. John Wiley & Sons: New York, 1999.
2. (a) Clode DM. Carbohydrate cyclic acetal formation and migration. Chemical Reviews 1979; 79: 491–513.
3. (b) Nicolaou KC, Daines RA, Uenishi J, et al. Total synthesis of amphoteronolide B and amphotericin B. 1. Strat-egy and stereocontrolled construction of key building blocks. Journal of the American Chemical Society 1988; 110(14): 4685–4696.
4. (c) Kim Y, Singer RA, Carreira EM. Total synthesis of macrolactin A with versatile catalytic, enantioselective dienolate aldol addition reactions. Angewandte Chemie International Editoin 1998; 37: 1261–1263.
5. Zhang Q, Kang X, Long L, et al. Mild and selective deprotection of tert-Butyl(dimethyl)silyl ethers with catalyt-ic amounts of sodium tetrachloroaurate(III) dihydrate. Synthesis 2015; 47: 55–64.
6. Khan AT., Mondal EA. Highly efficient and useful synthetic protocol for the cleavage of tert-Butyldimethylsilyl (TBS) ethers using a catalytic amount of acetyl chloride in dry methanol. Synlett, 2003, 694.
7. DiLauro AM., Seo W, Phillips ST. Use of catalytic fluoride under neutral conditions for cleaving silicon–oxygen bonds. Journal of Organic Chemistry 2011; 76: 7352–7358.
8. Corey EJ, Venkateswarlu A. Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. Journal of American Chemical Society 1972; 94: 6190–6191.
9. Chaudhary SK., Hernandez O. 4-dimethylaminopyridine: an efficient and selective catalyst for the silylation of alcohols. Tetrahedron Lett 1979; 20: 99–102.
10. Corey EJ, Cho H, Rucker C, et al. Studies with trialkylsilyltriflates: new syntheses and applications. Tetrahedron Lett 1981; 22: 3455–3458.
11. Lombardo L. Diisopropylethylamine: An effective catalyst for the introduction of the t-butyldimethylsilyl group. Tetrahedron Lett 1984; 25: 227–228.
12. Kocieñski PJ. Protecting Groups. Georg Thieme Verlag: New York, 1994.
13. Corey EJ, Snider BB. Total synthesis of (+-)-fumagillin. Journal of American Chemical Society 1972; 94: 2549–2550.
14. Pilcher AS, Hill DK, Shimshock SJ, et al. Selective deprotection of trialkylsilyl ethers using fluorosilicic acid. Journal of Organic Chemstry 1992; 57: 2492–2495.
15. Corey EJ, Yi KY. Tetrafluorosilane is a mild and very selective reagent for the cleavage of silyl-protected alcohols. Tetrahedron Letter 1992; 33: 2289–2290.
16. Corey EJ, Jones GB. Reductive cleavage of tert-butyldimethylsilyl ethers by diisobutylaluminum hydride. Jour-nal of Organic Chemstry 1992; 57: 1028–1029.
17. Tanemura K, Suzuki T, Horaguchi T. Deprotection of silyl ethers using 2,3-dichloro-5,6-dicyano-p-benzoquinone. Journal of Chemical Society 1992: 2997–2998.
18. Dutta Gupta A, Singh R, Singh VK. A mild and efficient method for the cleavage of tert Butyldimethylsilyl and Tetrahydropyranyl ethers by ceric ammonium nitrate in methanol. Synlett 1996; 69–71.
19. Lipshutz BH, Keith J. Selective deprotection of alkyl vs. aryl silyl ethers. Tetrahedron Letter 1998; 39: 2495–2498.
20. Oriyama T, Kobayashi Y, Noda K. Chemoselective and practical deprotection of alkyl trialkylsilyl ethers in the presence of aryl trialkylsilyl ethers by a catalytic amount of Sc(OTf)3 Synlett 1998: 1047–1048.
21. Bartoli G, Bosco M, Marcantoni E, et al. A mild, efficient, and selective method for the desilylation of more common Trialkylsilyl ethers by cerium(III) chloride heptahydrate and sodium iodide in acetonitrile. Synlett 1998: 209–211.
22. Karimi B, Zamani A, Zarayee D. N-Iodosuccinimide (NIS) as a mild and highly chemoselective catalyst for depro-tection of tert-butyldimethylsilyl ethers. Tetrahedron Letter 2004; 45: 9139–9141.
23. Kumar GDK, Baskaran S. A facile, catalytic, and environmentally benign method for selective deprotection of tert-Butyldimethylsilyl ether mediated by phosphomolybdic acid supported on silica gel. Journal of Organic Chemstry 2005; 70: 4520–4523.
24. Peng Y, Li WDZ. A mild and efficient desilylation of O-tert-Butyldimethylsilyl ethers mediated by chlorotrime-thylsilane and potassium fluoride dihydrate in acetonitrile. Synlett 2006: 1165–1168.
25. Shah STA, Singh S, Guiry PJ. A novel, chemoselective and efficient microwave-assisted deprotection of silyl ethers with selectfluor Journal of Organic Chemistry 2009; 74: 2179–2182.
26. ang B, Sun HX, Sun ZH. LiOAc-catalyzed chemoselective deprotection of aryl silyl ethers under mild conditions. Journal of Organic Chemical 2009; 74: 1781–1784.
27. Yeom CE, Kim HW, Lee SY, et al. DBU-Mediated mild and chemoselective deprotection of aryl silyl ethers and tandem biaryl ether formation. Synlett 2007, 146–150.
28. Raghavan S, Vinoth V, Raju Chowhan L. Highly stereoselective preparation of chiral α-substituted sulfides from α-chloro sulfides via 1,2-asymmetric induction. Synlett 2009; 12: 1807–1810.
29. Raghavan S, Raju Chowhan L. Stereoselective carbon–carbon bond formation via 1,2-asymmetric induction by a β-substituent in the reaction of α-chloro sulfides with organozinc reagents. Indian Journal of Chemistry 2018; 57B: 327–339.
30. Coste G, Gerber-Lemaire S. Selective hydrolysis of anti-1,3-diol-acetonides for the differentiation of 1,3-anti and 1,3-syn diols. Tetrahedron Lett 2006; 47:671–674.
31. Sabitha G, Reddy GSKK, Reddy KB, et al. Vanadium (III) chloride: A mild and efficient catalyst for the chemose-lective deprotection of acetonides. Journal of Molecular Catalysis A: Chemical 2005; 238: 229–232.
32. Reddy SM, Reddy YV, Venkateswarlu Y. A mild and efficient method for the chemoselective deprotection of ace-tonides with lanthanum (III) nitrate hexahydrate. Tetrahedron Letter 2005; 46: 7439–7441.
33. Yadav JS, Satyanarayana M, Raghavendra S, et al. Chemoselective hydrolysis of terminal isopropylidene acetals in acetonitrile using molecular iodine as a mild and efficient catalyst. Tetrahedron Letter 2005; 46: 8745–8748.
34. Chari MA, Syamasundar K. Polymer-supported ferric chloride as a heterogeneous catalyst for chemoselective deprotection of acetonides. Synthesis 2005: 708–710.
35. Cong X, Hu F, Liu KG, et al. Chemoselective deprotection of cyclic N, O-aminals using catalytic bismuth (III) bromide in acetonitrile. Journal of Organic Chemsitry 2005; 70: 4514–4516.
36. Chang CC, Liao BS, Liu ST. Deprotection of acetals and ketals in a colloidal suspension generated by sodium tetrakis (3,5-trifluoromethylphenyl) borate in water. Synlett 2007: 283–287.
37. Singh S, Duffy CD, Shah STA, et al. ZrCl4 as an efficient catalyst for a novel one-pot protection/deprotection synthetic methodology. Journal of Organic Chemistry 2008; 73: 6429–6432.
38. Maddani MR, Prabhu KR. Metal-free deprotection of terminal acetonides by using tert-butyl hydroperoxide in aqueous medium. Synlett 2011; 821–825.
39. Pfrengle F, Dekaris V, Schefzig L, et al. Indium trichloride mediated cleavage of acetonides in the presence of ac-id-labile functional groups - enhancing the synthetic utility of 1,3-dioxolanyl-substituted 1,2-oxazines. Synlett 2008; 2965–2968.
40. Inaba H, Ariyasu H, Okuhira H, et al. Endocrine dysfunctions during treatment of immune-checkpoint inhibitors. Trends in Immunotherapy 2020; 4(1): 18–26. doi: 10.24294/ti.v4.i1.606.
DOI: https://doi.org/10.24294/ace.v1i3.702
Refbacks
- There are currently no refbacks.
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.