Collagen cross-links: a convenient synthesis of tert-butyl-(2S)-2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate |
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Institution: | 1. Institute of Nuclear Chemistry and Technology, 16 Dorodna Street, 03-195 Warsaw, Poland;2. Centre of Molecular and Macromolecular Studies PAS, 112 Sienkiewicza Street, 90-363 Łódź, Poland;3. Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Street, 02-097 Warsaw, Poland;4. National Medicines Institute, 30/34 Chełmska Street, 00-723 Warsaw, Poland |
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Abstract: | An efficient synthesis of tert-butyl-(2S)-2-(tert-butoxycarbonyl)amino]-4-(2-oxiranyl) butanoate (5), the key intermediate for preparation of collagen cross-links (+)-pyridinoline (Pyd, 1) and (+)-deoxypyridinoline (Dpd, 2) was described from (4S)-5-(tert-butoxy)-4-(tert-butoxycarbonyl)amino]-5-oxopentanoic acid (6) in six steps. Also, an improved synthesis of iodide (2S)-(−)-4b was presented. |
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