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13
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0009479858
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note
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The syntheses were performed in a parallel array on a robotic liquid handler synthesizer (SOLARIS™). The additions, aspirations, and washings were performed using a robotic arm possessing four alternate aspirating and coaxial tips. The 4-(2′,4′-dimethoxyphenylfluorenylmethoxycarbonylaminomethyl)phenoxy polystyrene, 'Rink Amide resin', loaded at 0.6 mmol Fmoc-amine/gm was placed in a round bottomed flask and was subjected to Fmoc cleavage with 20% piperidine in DMF for 10 min. The resin was subjected to a series of washings (3x5 mL) with DMF, MeOH, and DCM. Subsequently, the next step was coupling of the HMBA to the resin using 3 equivalents of DIC, HOBt, and HMBA in DMA for 4 h. At this stage, the solvent was drained and each flask was subjected to standard washing cycles. The next step was the Mitsunobu C-C alkylation using fivefold excess of tributylphosphine, N,N,N′,N′ -tetramethylazodicarboxamide, and the active methylene compounds was conducted in dry THF at room temperature. After shaking the mixture for 12 h at room temperature, the reagents were drained and the resin was subjected to the washing cycles. Cleavage of products from the resin was performed with 20% TFA in DCM over 45 min at rt gave the desired compounds.
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14
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0009514196
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Structure of dimeric ester and the resultant Mitsunobu product product: (equation presented)
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Structure of dimeric ester and the resultant Mitsunobu product product: (equation presented)
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15
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84972809434
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Crowley, J. I.; Harvey, T. B.; Rapoport, H. J. Macromol. Sci. Chem. 1973, A7(5), 1117-1126.
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37049094373
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Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans, 1 1982, 2319.
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0031317101
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0003008165
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Yan, B.1
Sun, Q.2
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