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Diphenylmethylsilyl ether (DPMS): a protecting group for alcohols

Cite this: J. Org. Chem. 1987, 52, 1, 165–168
Publication Date (Print):January 1, 1987
https://doi.org/10.1021/jo00377a033
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    2. Tsuyoshi Mita, Yuki Higuchi, and Yoshihiro Sato . Carboxylation with CO2 via Brook Rearrangement: Preparation of α-Hydroxy Acid Derivatives. Organic Letters 2014, 16 (1) , 14-17. https://doi.org/10.1021/ol403099f
    3. Anthony M. DiLauro, Wanji Seo, and Scott T. Phillips . Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon–Oxygen Bonds. The Journal of Organic Chemistry 2011, 76 (18) , 7352-7358. https://doi.org/10.1021/jo200848j
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    5. Kyzgaldak Ramazanova, Soumyadeep Chakrabortty, Fabian Kallmeier, Nadja Kretzschmar, Sergey Tin, Peter Lönnecke, Johannes G. de Vries, Evamarie Hey-Hawkins. Access to Enantiomerically Pure P-Chiral 1-Phosphanorbornane Silyl Ethers. Molecules 2023, 28 (17) , 6210. https://doi.org/10.3390/molecules28176210
    6. Nnamdi Akporji, Josh Lieberman, Michael Maser, Masahiko Yoshimura, Zarko Boskovic, Bruce H. Lipshutz. Selective Deprotection of the Diphenylmethylsilyl (DPMS) Hydroxyl Protecting Group under Environmentally Responsible, Aqueous Conditions. ChemCatChem 2019, 11 (23) , 5743-5747. https://doi.org/10.1002/cctc.201901232
    7. Richard C. Larock, Anton V. Dubrovskiy, Nataliya A. Markina. Alkylation and Acylation of Aldehydes, Ketones, and Their Derivatives. 2018, 1-145. https://doi.org/10.1002/9781118662083.cot08-013
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    13. Heather K. Baker, Aaron M. Hartel. Preparation of proximal β-hydroxy silyl enol ethers from α,β-epoxyketones using silyllithium reagents. Tetrahedron Letters 2009, 50 (28) , 4012-4014. https://doi.org/10.1016/j.tetlet.2009.04.085
    14. Gerald L. Larson, Andreas Luxenburger. Methyldiphenylchlorosilane. 2008https://doi.org/10.1002/047084289X.rm182f.pub2
    15. Sabita Patel, B.K. Mishra. Chromium(VI) oxidants having quaternary ammonium ions: studies on synthetic applications and oxidation kinetics. Tetrahedron 2007, 63 (21) , 4367-4406. https://doi.org/10.1016/j.tet.2007.02.073
    16. Arturo Battaglia, Eleonora Baldelli, Ezio Bombardelli, Giacomo Carenzi, Gabriele Fontana, Maria Luisa Gelmi, Andrea Guerrini, Donato Pocar. Selective synthesis of 14β-amino taxanes. Tetrahedron 2005, 61 (32) , 7727-7745. https://doi.org/10.1016/j.tet.2005.05.087
    17. R. David Crouch. Selective monodeprotection of bis-silyl ethers. Tetrahedron 2004, 60 (28) , 5833-5871. https://doi.org/10.1016/j.tet.2004.04.042
    18. Angel M Montaña, Pedro M Grima. Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature. Tetrahedron 2002, 58 (24) , 4769-4786. https://doi.org/10.1016/S0040-4020(02)00452-0
    19. Maria N. Bakola‐Christianopoulou. Silylation–desilylation of quinones and their derivatives. Applied Organometallic Chemistry 2001, 15 (11) , 889-900. https://doi.org/10.1002/aoc.231
    20. Gerald L. Larson. Methyldiphenylchlorosilane. 2001https://doi.org/10.1002/047084289X.rm182f
    21. Ahmad Shaabani, Ali-Reza Karimi. OXIDATION DEPROTECTION OF TRIMETHYLSILYL ETHERS TO CARBONYL COMPOUNDS BY NaBrO 3 -NH 4 Cl REAGENT IN AQUEOUS ACETONITRILE. Synthetic Communications 2001, 31 (5) , 759-765. https://doi.org/10.1081/SCC-100103266
    22. Michael A. Brook, Sonya Balduzzi, Mustafa Mohamed, Christine Gottardo. The photolytic and hydrolytic lability of sisyl (Si(SiMe3)3) ethers, an alcohol protecting group. Tetrahedron 1999, 55 (33) , 10027-10040. https://doi.org/10.1016/S0040-4020(99)00562-1
    23. Dieter Enders, Peter Fey, Thomas Schmitz, Braj Bhushan Lohray, Bernd Jandeleit. Regio- and stereoselective a4-umpolung reactions of α,β-unsaturated esters to 1,6-dicarbonyl compounds by addition of enantiopure nucleophiles to racemic tetracarbonyl (η3-alyl)iron(1+) complexes. Journal of Organometallic Chemistry 1996, 514 (1-2) , 227-232. https://doi.org/10.1016/0022-328X(95)06042-U
    24. H. Firouzabadi, F. Shiriny. Bis[Trinitrato Cerium(IV)] Chromate; [(NO 3 ) 3 Ce] 2 CrO 4 vs Trinitrato Cerium(IV) Chromate Dihydrate; [(NO 3 ) 3 Ce] CrO 4 .2H 2 O in the oxidation of trimethylsilyl ethers. Synthetic Communications 1996, 26 (4) , 649-655. https://doi.org/10.1080/00397919608086737
    25. Martin Wills, Ernest W. Colvin. Alkylboron and -silicon Compounds. 1995, 513-547. https://doi.org/10.1016/B0-08-044705-8/00266-1
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    27. Ernest W. Colvin. Silicon. 1995, 313-354. https://doi.org/10.1016/B978-008046519-7.00098-8
    28. Derrick L.J. Clive, Yong Tao, Ahmad Khodabocus, Yong-Jin Wu, A. Gaëtan Angoh, Sharon M. Bennett, Christopher N. Boddy, Luc Bordeleau, Michel Cantin, David R. Cheshire, Dorit Kellner, Galit Kleiner, Donald S. Middleton, Christopher J. Nichols, Scott R. Richardson, Lu Set, Peter G. Vernon. Total synthesis of crystalline (±)-fredericamycin A. 1995, 27-74. https://doi.org/10.1016/S1572-5995(06)80052-9
    29. Olivier Piva, Aicha Amougay, Jean-Pierre Pete. Selective Deprotection of Diphenylmethylsilylethers of Allylic and Benzylic Alcohols. Synthetic Communications 1995, 25 (2) , 219-226. https://doi.org/10.1080/00397919508010810
    30. Derrick L.J. Clive, Nola Etkin. Synthesis of α-amino acids by addition of putative azido radicals to α-methoxy acrylonitriles derived from aldehydes and ketones. Tetrahedron Letters 1994, 35 (16) , 2459-2462. https://doi.org/10.1016/S0040-4039(00)77143-7
    31. H. Firouzabadi, I. Mohammadpoor-Baltork. Lewis Acid Promoted Reactions. (IV.) 1a,b Oxidation Deprotection of Trimethylsilyl Ethers with Silver and Sodium Bromates; AgBrO 3 , NaBrO 3. Synthetic Communications 1994, 24 (8) , 1065-1077. https://doi.org/10.1080/00397919408011700
    32. Bernhard Boddenmann, Reinhart Keese. Synthesis of cyclododeca-2,8-diyne-1,7-dione. Tetrahedron Letters 1993, 34 (9) , 1467-1470. https://doi.org/10.1016/S0040-4039(00)60320-9
    33. Bruce H. Lipshutz, Saumitra Sengupta. Organocopper Reagents: Substitution, Conjugate Addition, Carbo/Metallocupration, and Other Reactions. 1992, 135-631. https://doi.org/10.1002/0471264180.or041.02
    34. Corinne Brouard, Jacques Pornet, Léone Miginiac. (2E, 4E)-1,6 bistrimethylsilylhexa-2,4 -diene: application a la synthese de 3,4-divinyloxolanes. Tetrahedron 1992, 48 (12) , 2385-2400. https://doi.org/10.1016/S0040-4020(01)88759-7
    35. . Preparation of Alcohols. 1992, 15-58. https://doi.org/10.1002/9780470126004.ch3
    36. Uwe Weinzierl, Wolfgang Seidel. Untersuchungen zu Mesityldimethylhalogensilanen als Schutzgruppenreagenzien für Alkohole. Journal für Praktische Chemie 1991, 333 (6) , 917-922. https://doi.org/10.1002/prac.19913330615
    37. Gerald L. Larson. Silicon - the silicon-carbon bond: Annual survey for the year 1987. Journal of Organometallic Chemistry 1989, 374 (1-3) , 1-347. https://doi.org/10.1016/0022-328X(84)85001-9
    38. Gerald L. Larson, Reyes Berrios, Jose A. Prieto. A regio- and stereoselective synthesis of (Z) enol methyldiphenylsilyl ethers. Tetrahedron Letters 1989, 30 (3) , 283-286. https://doi.org/10.1016/S0040-4039(00)95180-3
    39. . CARBON-CARBON BOND FORMING REACTIONS. 1988, 1-233. https://doi.org/10.1016/B978-0-12-040818-4.50007-5
    40. . PROTECTING GROUPS. 1988, 359-375. https://doi.org/10.1016/B978-0-12-040818-4.50011-7
    41. Véronique Bolitt, Charles Mioskowski, Dong-Soo Shin, J.R. Falck. Triphenylphosphine hydrobromide: A mild and efficient catalyst for tetrahydropyranylation of tertiary alcohols. Tetrahedron Letters 1988, 29 (36) , 4583-4586. https://doi.org/10.1016/S0040-4039(00)80553-5
    42. S. E. DENMARK, R. P. HAMMER, E. J. WEBER, K. L. HABERMAS. ChemInform Abstract: Diphenylmethylsilyl Ether (DPMS): A Protecting Group for Alcohols.. ChemInform 1987, 18 (28) https://doi.org/10.1002/chin.198728232
    43. Hideo Iio, Tsukasa Mizobuchi, Takashi Tokoroyama. High diastereoselectivity observed in the vinylation reaction of α,β-epoxy aldehydes with β-silylphosphorous ylide. Tetrahedron Letters 1987, 28 (21) , 2379-2382. https://doi.org/10.1016/S0040-4039(00)96129-X

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