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Scheme 2 | Sustainable Chemical Processes

Scheme 2

From: An astute synthesis of locked nucleic acid monomers

Scheme 2

Convergent synthesis of LNA monomers [ 10 ]. Reagents (% yields): (i) BnBr, NaH, DMF (71%); (ii) (a) Ac2O, Pyridine; (b) 80% AcOH; (c) Ac2O, Pyridine (77%); (iii) nucleobase, N,O-bis(trimethylsilyl)acetamide, TMS-triflate, CH3CN or 1,2-dichloroethane (13a, 75%; 13b, 76%; 13c, 52%; 13d, 74%); (iv) NaOMe, MeOH (14a, 95%; 14b, 97%; 14c, 73%; 14d, 54%); (v) (a) TsCl, Pyridine; (b) NaH, DMF (15a, 30%; 15b, 42%; 15c, 44%; 15d, 51%); (vi) 20% Pd(OH)2-C, H2, EtOH (1a, 78%; 1b, 98%); BCl3, DCM (1c, 84%); 10% Pd-C, 1,4-cyclohexadiene, MeOH (1d, 36%).

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