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

Scheme 4. Synthesis of 3-C-(Glycopyranosyl)1-propoxyphthalimide (1–12) Precursors of 1,6-Dioxaspiro[4.5]decane Structures.

Scheme 4

Reagents and conditions: (a) (i) BH3•THF 1 M complex, THF, 0 °C to rt, 1 h. (ii) NaOH 3 M, H2O2 30%, 0 °C, 1 h. (b) HONPhth, Ph3P, DEAD, THF, 0 °C to rt, 1–4 h. (c) Ac2O, Py, DMAP, 0 °C to rt, 1 h. (d) ClPO(OPh)2, DMAP, CH2Cl2, 0 °C to rt, 2 h. (e) (i) I2, CH2Cl2, rt, 3 h. (ii) Zn dust, AcOH, Et2O:MeOH, rt, overnight. (f) (i) allyltrimethylsilane, BF3•Et2O, CH3CN, 0 °C to rt, 1.5 h. (ii) Na2CO3, MeOH, rt, 2.5 h. (iii) PhCH(OMe)2, CSA, DMF, rt, overnight. (g) (i) HONPhth, Ph3P, DEAD, THF, 0 °C to rt, 0.5 h. (ii) ClPO(OPh)2, DMAP, CH2Cl2, 0 °C to rt, 1.5 h. (h) TFA/H2O, CH2Cl2, 0 °C to rt, 1 h.

Values in parentheses are isolate yields.