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. 2019 Apr 12;84(10):6143–6157. doi: 10.1021/acs.joc.9b00338

Scheme 1. Synthesis of Modified Terminal Riboses 9 and 10.

Scheme 1

Reagents and conditions: (a) 5-Ph-1-H-tetrazole, dibenzyl N,N-diisopropylphosphoramidite, DCM, 20 °C, 1 h; (b) triethylamine, H2O2, 0–20 °C, 1 h; (c) hydrogen (balloon), Pd/C, 5 h, TEAB (1 M), 20 °C; (d) Dowex D50 (H+), tributylamine; (e) tritylchloride, pyridine, 20 °C, 16 h; (f) sodium borohydride, ethanol, 0–20 °C, 2 h; (g) tosyl chloride, pyridine, 60 °C, 16 h; (h) HCOOH/diethylether, 20 °C, 16 h; (i) 5-Ph-1-H-tetrazole, di-tert-butyl N,N-diisopropylphosphoramidite, DCM, 20 °C, 1 h; (j) triethylamine, H2O2, 0–20 °C, 1 h; (k) aqueous TFA, 0–20 °C, 4 h; (l) Dowex D50 (H+), tributylamine.