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. 2020 Jul 27;85(16):10891–10901. doi: 10.1021/acs.joc.0c01459

Scheme 2. Synthetic Pathway of Compounds 814.

Scheme 2

Reagents and conditions: (a) HBr, r.t., 12 h; (b) (1) SOCl2, dry DMF, r.t. 2 h; (2) Dry MeOH, Et3N, r.t. 2 h; (c) 95% H2NNH2·xH2O/KOH, TEG, 150–200 °C, 24 h; (d) peracetylated glucosyl bromide, K2CO3/TBAB/CH2Cl2/H2O, reflux, 24 h; (e) Et3N/MeOH/H2O/hexane, r.t. 48 h; (f) LiAlH4 in THF 2 M, THF dry, r.t. 3 h; (g) Et2O, oxalyl chloride 0 °C → r.t. 30 min.