A deprotection procedure using SO₃H silica gel to remove non-silyl protecting groups

References

• Wuts, P. G. M . Greene's Protective Groups in Organic Synthesis, 5th ed.; John Wiley & Sons: Hoboken, New Jersey, 2014.
   Google Scholar
• Kocienski, P. J . Protecting Groups, 3rd ed.; Thieme: New York, 2005.
   Google Scholar
• Maehara, T. ; Motoyama, K. ; Toma, T. ; Yokoshima, S. ; Fukuyama, T . Total Synthesis of (−)‐Tetrodotoxin and 11‐norTTX‐6(R)‐ol. Angew. Chem. Int. Ed. 2017, 56 ,1549-1552. DOI: 10.1002/anie.201611574.
   PubMed Web of Science ®Google Scholar
• Uesugi, S.-I. ; Watanabe, T. ; Imaizumi, T. ; Ebisu, H. ; Chinen, T. ; Nagumo, Y. ; Shibuya, M. ; Kanoh, N. ; Usui, T. ; Iwabuchi, Y . Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B. J. Org. Chem. 2015, 80 ,12333-12350. DOI: 10.1021/acs.joc.5b02256.
   PubMed Web of Science ®Google Scholar
• Dayaker, G. ; Durand, T. ; Balas, L . Total Synthesis of Neuroprotectin D1 Analogues Derived from Omega-6 Docosapentaenoic Acid (DPA) and Adrenic Acid (AdA) from a Common Pivotal, Late-Stage Intermediate. J. Org. Chem. 2014, 79 ,2657-2665. DOI: 10.1021/jo500147r.
   PubMed Web of Science ®Google Scholar
• Kuntiyong, P. ; Lee, T. H. ; Kranemann, C. L. ; White, J. D . Total Synthesis of the Marine Toxin Phorboxazole a Using Palladium(II)-Mediated Intramolecular Alkoxycarbonylation for Tetrahydropyran Synthesis. Org. Biomol. Chem. 2012, 10 ,7884-7899. DOI: 10.1039/c2ob25766a.
   PubMed Web of Science ®Google Scholar
• An, C. ; Hoye, A. T. ; Smith, A. B. III. Total Synthesis of (−)-Irciniastatin B and Structural Confirmation via Chemical Conversion to (+)-Irciniastatin A (Psymberin). Org. Lett. 2012, 14 ,4350-4353. DOI: 10.1021/ol301783p.
   PubMed Web of Science ®Google Scholar
• Stahl, G. L. ; Walter, R. ; Smith, C. W . General Procedure for the Synthesis of Mono-N-Acylated 1,6-Diaminohexanes. J. Org. Chem. 1978, 43 ,2285-2286. DOI: 10.1021/jo00405a045.
   Web of Science ®Google Scholar
• McOmie, J. F. W. ; West, D. E . 3,3'-DIHYDROXYBIPHENYL [m,m'-Biphenol]. Org. Synth. 1969, 49 ,50-52. DOI: 10.15227/orgsyn.049.0050.
   Google Scholar
• Plattner, J. J. ; Gless, R. D. ; Rapoport, H . Synthesis of Some DE and CDE Ring Analogs of Camptothecin. J. Am. Chem. Soc. 1972, 94 ,8613-8615. DOI: 10.1021/ja00779a072.
   PubMed Web of Science ®Google Scholar
• Carpino, L. ; Han, G . 9-Fluorenylmethoxycarbonyl Amino-Protecting Group. J. Org. Chem. 1972, 37 ,3404-3409. DOI: 10.1021/jo00795a005.
   Web of Science ®Google Scholar
• Oikawa, Y. ; Yoshioka, T. ; Yonemitsu, O . Specific Removal of o-Methoxybenzyl Protection by DDQ Oxidation. Tetrahedron Lett 1982, 23 ,885-888. DOI: 10.1016/S0040-4039(00)86974-9.
   Web of Science ®Google Scholar
• Wang, Y. ; Babirad, S. A. ; Kishi, Y . Preferred Conformation of C-Glycosides. 8. Synthesis of 1,4-Linked Carbon Disaccharides. J. Org. Chem. 1992, 57 ,468-481. DOI: 10.1021/jo00028a017.
   Web of Science ®Google Scholar
• Heathcock, C. H. ; Ratcliffe, R . Stereoselective Total Synthesis of the Guaiazulenic Sesquiterpenoids α-Bulnesene and Bulnesol. J. Am. Chem. Soc. 1971, 93 ,1746-1757. DOI: 10.1021/ja00736a029.
   Web of Science ®Google Scholar
• Sakaitani, M. ; Hori, K. ; Ohfune, Y . One-Pot Conversion of N-Benzyloxycarbonyl Group into N-Tert-Butoxycarbonyl Group. Tetrahedron Lett 1988, 29 ,2983-2984. DOI: 10.1016/0040-4039(88)85064-0.
   Web of Science ®Google Scholar
• Sasaki, T. ; Minamoto, K. ; Itoh, H . Convenient Synthesis of Some Purine 8,5'-Imino Cyclonucleosides. J. Org. Chem. 1978, 43 ,2320-2325. DOI: 10.1021/jo00406a003.
   Web of Science ®Google Scholar
• Fukuyama, T. ; Jow, C. K. ; Cheung, M . 2- and 4-Nitrobenzenesulfonamides: Exceptionally Versatile Means for Preparation of Secondary Amines and Protection of Amines. Tetrahedron Lett. 1995, 36 ,6373-6374. DOI: 10.1016/0040-4039(95)01316-A.
   Web of Science ®Google Scholar
• Corey, E. J. ; Venkateswarlu, A . Protection of Hydroxyl Groups as Tert-Butyldimethylsilyl Derivatives. J. Am. Chem. Soc. 1972, 94 ,6190-6191. DOI: 10.1021/ja00772a043.
   Web of Science ®Google Scholar
• Fujii, H. ; Yamada, T. ; Hayashida, K. ; Kuwada, M. ; Hamasaki, A. ; Nobuhara, K. ; Ozeki, S. ; Nagase, H . Application of SO3H Silica Gel to Deprotection of Silyl Ethers. Heterocycles 2012, 85 ,2685-2691. DOI: 10.3987/COM-12-12577.
   Web of Science ®Google Scholar
• Fujii, H. ; Shimada, N. ; Ohtawa, M. ; Karaki, F. ; Koshizuka, M. ; Hayashida, K. ; Kamimura, M. ; Makino, K. ; Nagamitsu, T. ; Nagase, H . Deprotection of Silyl Ethers by Using SO3H Silica Gel: Application to Sugar, Nucleoside, and Alkaloid Derivatives. Tetrahedron 2017, 73 ,5425-5429. DOI: 10.1016/j.tet.2017.07.047.
   Web of Science ®Google Scholar
• The esters here were prepared according to the following literatures . ( a ) Roy, O. ; Riahi, A. ; Hénin, F. ; Muzart, J . Catalysed Asymmetric Protonation of Simple Linear Keto-Enolic Species - a Route to Chiral α-Arylpropionic Acids. Eur. J. Org. Chem 2002, 2002 ,3986-3994. DOI: 10.1002/1099-0690(200212)2002:23 < 3986::AID-EJOC3986 > 3.0.CO;2-L; (b) Sadeghian, H. ; Attaran, N. ; Jafari, Z. ; Saberi, M. R. ; Pordel, M. ; Riazi, M. M . Design and Synthesis of 4-Methoxyphenylacetic Acid Esters as 15-Lipoxygenase Inhibitors and SAR Comparative Studies of Them. Bioorg. Med. Chem 2009, 17 ,2327-2335. DOI: 10.1016/j.bmc.2009.02.009. (c) Revelant, G. ; Dunand, S. ; Hesse, S. ; Kirsch, G . Microwave-Assisted Synthesis of 5-Substituted 2-Aminothiophenes Starting from Arylacetaldehydes. Synthesis 2011, 18 ,2935-2940. DOI: 10.1055/s-0030-1261032. DOI: 10.1002/1099-0690(200212)2002:23<3986::AID-EJOC3986>3.0.CO;2-L.
   Web of Science ®Google Scholar
• Meier, C. ; Ruppel, M. F. H. ; Vukadinović, D. ; Balzarini, J . Second Generation of cycloSal-Pronucleotides with Esterase-Cleavable Sites: The "Lock-In” -Concept. Nucleosides Nucleotides Nucleic Acids 2004, 23 ,89-115. DOI: 10.1081/NCN-120027820.
   PubMed Web of Science ®Google Scholar
• Fleming, P. ; O’Shea, D. F . Controlled Anion Migrations with a Mixed Metal Li/K-TMP Amide: General Application to Benzylic Metalations. J. Am. Chem. Soc. 2011, 133 ,1698-1701. DOI: 10.1021/ja110234v.
   PubMed Web of Science ®Google Scholar
• Grestenberger, B. S. ; Konopeiski, J. P . tert-Buyldiphenylsilylethyl (“TBDPSE”): A Practical Protecting Group for Phenols. J. Org. Chem. 2005, 70 ,1467-1470. DOI: 10.1021/jo048192u Tetrabutylammoniumfluoride, the gold standard to.
   PubMed Web of Science ®Google Scholar