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. 2013 Dec 4;56(24):10079–10102. doi: 10.1021/jm401497a

Scheme 5. Synthesis of Acyclic-ADPR.

Scheme 5

Reagents and conditions: (i) DBU, DMF, 60 °C, 16 h, 48%; (ii) MeOH/NH3, 80 °C, 16 h, 88%; (iii) POCl3, TEP, 0 °C, 1 h, 72%; (iv) morpholine, dipyridyl disulfide, PPh3, DMSO, rt, 1 h then β-NMN+, MgSO4, 0.2 M MnCl2; (v) NADase, Tris buffer (0.1M, pH 7.3), rt, 81% for steps iv–v.