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. 2022 Dec 8;131:106316. doi: 10.1016/j.bioorg.2022.106316

Scheme 1.

Scheme 1

Reagents and conditions: (a) BnBr, K2CO3, DMF; (b) benzyl 2, 2, 2-trichloroacetimidate, TfOH, CH2Cl2; (c) LiOH, THF-MeOH-H2O; (d) TMSOTf, 4 Å Ms, CH2Cl2; (e) CH3ONa, MeOH; (f) PivCl, CH2Cl2; (g) (i) TMSOTf, 4 Å Ms, CH2Cl2; (ii) NaOH, MeOH-THF-H2O; (h) 10 % Pd/C, H2, MeOH-THF; (i) (i) Ac2O, DMAP, pyridine; (j) (i) various bromide alkanes, K2CO3, DMF; (ii) CH3ONa, MeOH; (k) (i) (COCl)2, CH2Cl2 (ii) R1R2N•HCl, Et3N, CH2Cl2; (iii) CH3ONa, CH3OH.