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The low yield clearly results from hydrolysis of both ester groups. These groups have shown quite similar reactivities in reaction with a series of base catalysts that were used in an attempt to achieve chemoselective cleavage (via base-catalyzed elimination) of the acetyl group. Along these lines both DBU and Verkade's Superbase (Ilancumaran, P.; Verkade, J. G. J. Org. Chem. 1999, 64, 3086-3089) failed to improve the yield of compound 10.
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The low yield clearly results from hydrolysis of both ester groups. These groups have shown quite similar reactivities in reaction with a series of base catalysts that were used in an attempt to achieve chemoselective cleavage (via base-catalyzed elimination) of the acetyl group. Along these lines both DBU and Verkade's Superbase (Ilancumaran, P.; Verkade, J. G. J. Org. Chem. 1999, 64, 3086-3089) failed to improve the yield of compound 10.
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0001755181
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We have found that the combination of tert-butylamine/methanol gives better results than the methods previously used for hydrolysis of methoxyacetyl esters, including catalysis with ytterbium(III) triflate: Hanamoto, T, Sugimoto, Y, Yokoyama, Y, Inanaga, J. J. Org. Chem. 1996, 61, 4491-4492
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We have found that the combination of tert-butylamine/methanol gives better results than the methods previously used for hydrolysis of methoxyacetyl esters, including catalysis with ytterbium(III) triflate: Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491-4492.
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33847636412
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The reaction conditions that have been reported for acylation of lysophosphatidylcholines generally required a large (5- to 10-fold) excess of acylating agent; see ref 18a,b for detailed discussion
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The reaction conditions that have been reported for acylation of lysophosphatidylcholines generally required a large (5- to 10-fold) excess of acylating agent; see ref 18a,b for detailed discussion.
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41
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0032741250
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Compound 17 was completely hydrolyzed by phospholipase A2 from bee venom to give lysophosphatidylcholine 12b and 12-N-(5′- dimethylaminonaphthalene-1′-sulfonyl)aminododecanoic acid under the assay conditions previously reported: Roodsari, F. S.; Wu, D.; Pum, G. S.; Hajdu, J. J. Org. Chem. 1999, 64, 7727-7737.
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Compound 17 was completely hydrolyzed by phospholipase A2 from bee venom to give lysophosphatidylcholine 12b and 12-N-(5′- dimethylaminonaphthalene-1′-sulfonyl)aminododecanoic acid under the assay conditions previously reported: Roodsari, F. S.; Wu, D.; Pum, G. S.; Hajdu, J. J. Org. Chem. 1999, 64, 7727-7737.
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