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Converting the alcohol to a good leaving group using p-toluene-sulfonyl chloride, methanesulfonyl chloride, or trifluoromethane-sulfonic anhydride resulted in lower yields favoring the elimination product. Other nitrogen sources (tetramethylguanadinium azide, benzylamine, phthalimide) did not improve the yield.
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35
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0038614076
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Norcarane (Bicyclo[4.1.0]heptane)
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Wiley: New York, Collect.
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For the preparation of the Zn-Cu couple, see: Smith, R. D.; Simmons, H. E. Norcarane (Bicyclo[4.1.0]heptane). Organic Syntheses; Wiley: New York, 1973; Collect. Vol. No. V, pp 855-858. Alternatively, Zn dust (Aldrich, -325 mesh/<10 μm) can also be used to achieve similar results.
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Synthetic Studies on β-Lactam Antibiotics. VII. Mild removal of the Benzyl Ester Protecting Group with Aluminum Trichloride
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3 at 50°C for 5 h according to Tsuji, T.; Kataoka, T.; Yoshioka, M.; Sendo, Y.; Nishitani, Y.; Hirai, S.; Maeda, T.; Nagata, W. Synthetic Studies on β-Lactam Antibiotics. VII. Mild removal of the Benzyl Ester Protecting Group with Aluminum Trichloride. Tetrahedron Lett. 1979, 30, 2793-6.
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Rhodium-Catalyzed Nuclear Hydrogenation of α-Substituted Benzyl Alcohols and Esters. A Useful Procedure for Establishing Configurations
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This compound was prepared by catalytic hydrogenation of the parent unsubstituted cyclic urea used to prepare DMP 323 according to Stocker, J. H. Rhodium-Catalyzed Nuclear Hydrogenation of α-Substituted Benzyl Alcohols and Esters. A Useful Procedure for Establishing Configurations. J. Org. Chem. 1962, 27, 2288-9.
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Potency and Selectivity of Inhibition of the HIV Protease by a Small Nonpeptide Cyclic Urea, DMP 323
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Erickson-Viitanen, S.; Klabe, R. M.; Cawood, P. G.; O'Neal, P. L.; Meek, J. L. Potency and Selectivity of Inhibition of the HIV Protease by a Small Nonpeptide Cyclic Urea, DMP 323. Antimicrob. Agents Chemother. 1994, 38, 1628-34.
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An Assay for HIV RNA in Infected Cell Lysates, and Its Use for the Rapid Evaluation of Antiviral Efficacy
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Bacheler, L. T.; Paul, M.; Jadhav, P. K.; Otto, M.; Stone, B.; Miller, J. An Assay for HIV RNA in Infected Cell Lysates, and Its Use for the Rapid Evaluation of Antiviral Efficacy. Antiviral Chem. Chemother. 1994, 5 (2), 111-21.
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