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1
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0009680449
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3
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(a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. W.; Xu, D.; Zhang, X.L. J. Org. Chem. 1992, 57, 2768.
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18
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0009749323
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note
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All new compounds were characterized by full spectroscopic (NMR, low/high resolution MS) data. Yields refer to spectroscopically and chromatographically homogenous (≥95% by HPLC, TLC) materials.
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19
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23
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0009679933
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note
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The e.e. values reported for the diol adducts 3a-c were determined by chiral HPLC using an analytical Chiracel AD column, eluting with an isopropanol, hexane 40-60% gradient, 0.5 mL/min flow rate. The assignment of absolute stereochemistry follows from application of the Sharpless pneumonic (ref 6a). Furthermore, 4b and 5b were elaborated into active thrombin inhibitors with α-(R)-hydroxy quaternary lactam stereochemistry, which is deemed essential for high potency due to optimal binding at S3 of the thrombin active site (cf. ref 1, 3, and 4).
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24
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84989500123
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"Fortified" AD-mix is prepared by increasing the catalyst and chiral ligand loading of commercial AD-mix: (a) Walsh, P. J.; Sharpless, K. B. Synlett. 1993, 605.
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