-
3
-
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85037780439
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-
note
-
The following abbreviations are used throughout this account: ACN, acetonitrile; AcCl, acetyl chloride; Abz, 4-acetoxybenzyl; TBS, tertbutyldimethylsilyl; TBDPS, tert-butyldiphenylsilyl; DCA, dichloroacetic acid; DCM, dichloromethane; DCI, 4,5-dicyanoimidazole; DMT PASS, dimethoxytrityl resin product anchored sequential synthesis; DMF, dimethylformamide; DIPA, diisopropylamine; DIPEA, diisopropylethylamine; EtOAc, ethyl acetate; HPLC, high-pressure liquid chromatography; LC/ MS, liquid chromatography/mass spectrometric; MMT, monomethoxytrityl; NPE, 4-nitrophenethyl; TBAP, tetrabutylammonium periodate; v/v volume/volume.
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-
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4
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84962724341
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US Patent 5,874,532, Issued February 3, 1999
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(a) Pieken, W. P.; Gold, L. "Method for solution phase synthesis of oligonucleotides and peptides." US Patent 5,874,532, Issued February 3, 1999.
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Method for Solution Phase Synthesis of Oligonucleotides and Peptides
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Pieken, W.P.1
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5
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85037783045
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Pieken, W.1
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6
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85037776718
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note
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Bz).
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-
-
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7
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33847797467
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The polystyrene support employed in these studies was prepared according to the protocol of Farrall and Fréchet
-
The polystyrene support employed in these studies was prepared according to the protocol of Farrall and Fréchet (Farrall, M. J.; Fréchet, J. M. J. J. Org. Chem. 1976, 41, 3877-3882).
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85037763532
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note
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Typically, considerably larger excesses (up to 15 equiv vs 1-2 equiv) of MMT resin-bound amidites were required to accomplish full conversion of fully protected oligonucleotide substrates.
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Schirmeister, H.; Pfleiderer, W. Helv. Chim. Acta 1994, 77, 11. For a review on the use of the 4-nitrophenethyl protecting group in oligonucleotide chemistry, see: Pfleiderer, W.; Himmelsbach, F.; Charubala, R.; Schirmeister, H.; Beiter, A.; Schulz, B.; Trichtinger, T. Nucleosides Nucleotides 1985, 4, 81.
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Schirmeister, H.; Pfleiderer, W. Helv. Chim. Acta 1994, 77, 11. For a review on the use of the 4-nitrophenethyl protecting group in oligonucleotide chemistry, see: Pfleiderer, W.; Himmelsbach, F.; Charubala, R.; Schirmeister, H.; Beiter, A.; Schulz, B.; Trichtinger, T. Nucleosides Nucleotides 1985, 4, 81.
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85037770554
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note
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In fact, a tetrameric H-phosphonate substrate was prepared by successive application of the phenyl H-phosphonate resin DMT PASS method, and this compound did show a tendency to "oil out" in the extractive purification step.
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33
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