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. 2021 Sep 23;86(21):14508–14552. doi: 10.1021/acs.joc.1c01376

Scheme 5. Synthesis of 3-C-(α-d-Ribofuranosyl)1-propoxyphthalimide (13–15) Precursors of 1,6-Dioxaspiro[4.4]nonane Structures.

Scheme 5

Reagents and conditions: (a) DPSCl, imidazole, DMF, 0 °C, 0.5 h. (b) (i) BH3•THF 1 M complex, THF, 0 °C to rt, 2.5 h. (ii) NaHCO3, H2O2 30%, 0 °C, 1 h. (c) (i) HONPhth, Ph3P, DEAD, 50 °C, 2 h. (ii) Ac2O, DMAP, Py, rt, 1 h. (d) (i) HONPhth, Ph3P, DEAD, 50 °C, 2 h. (ii) Tf2O, Py, rt, 1 h. (e) 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane, Py, 0 °C, 20 h. (f) HONPhth, Ph3P, DEAD, 50 °C, overnight. (g) ClPO(OPh)2, DMAP, CH2Cl2, rt, 3 h.

Values in parentheses are isolate yields.