Synthesis of ester, glucoside and glucuronide prodrugs.
- Dawn M. George (1692688)
- Raymond J. Huntley (2524474)
- Kevin Cusack (5728823)
- David B. Duignan (1692706)
- Michael Hoemann (5728826)
- Jacqueline Loud (5728829)
- Regina Mario (5544320)
- Terry Melim (5330360)
- Kelly Mullen (5728832)
- Gagandeep Somal (5728835)
- Lu Wang (45927)
- Jeremy J. Edmunds (1692718)
Publication date
September 2018
DOI Publisher
Public Library of Science (PLoS)Abstract
Reagents and conditions: (a) 2-(dimethylamino)acetic acid, EDC, DMAP, DCM, rt, 92%; (b) Boc-(D)-valine, EDC, DMAP, DCM, rt, 72%; (c) TFA, DCM, 0°C to rt, 73% (d) 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate, BF3.OEt2, -78°C to rt, DCM, 95%; (e) Pd/C, H2 (10 bar), rt, 30% 9, 17% 10; (f) (2R,3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate, AgOTf, DCM, 5°C to rt, 7%; (g) LiOH, THF/H2O, 0°C, 50%.</p
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