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. Author manuscript; available in PMC: 2020 Feb 14.
Published in final edited form as: J Med Chem. 2019 Jan 3;62(3):1502–1522. doi: 10.1021/acs.jmedchem.8b01662

Scheme 2.

Scheme 2.

Synthesis of ribose derivatives containing the novel N6-dicyclobutylmethyl group and optionally substituted at the 5′ position with chloro or an alkyl thioether. Reagents and conditions: (i) dicyclobutylmethyl-amine, DIPEA, 2-propanol, rt; (ii) NH3/MeOH, rt; (iii) 2,2-dimethoxy propane, p-TSA, acetone, rt; (iv) SOCl2, pyridine, CH3CN, 0 oC-rt; (v) EtSNa, DMF, rt; (vi) 10% TFA, MeOH, 70 oC.