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. 2014 May 22;21(5):689–699. doi: 10.1016/j.chembiol.2014.03.009

Figure 3.

Figure 3

Chemical Syntheses

(A) Syntheses of 2-O-Bz-InsP5 (4) and 2-O-But-InsP5 (5).

(B) Syntheses of 2-O-Bn-InsP5(7), 2-O-Bn-5-PP-InsP4 (8), 5-PP-InsP4 (9), and 2,5-di-O-Bn-InsP4 (10). Reagents and conditions: (a) TFA:H2O, 10:1; (b) (BnO)2PN(iPr)2, 5-phenyl-1-H-tetrazole, DCM; (c) mCPBA, −40°C to room temperature; (d) Pd(OH)2, H2, MeOH, H2O; (e) BnBr, NaH, DMF; (f) aq TFA (90%):DCM, 1:1; (g) (NCCH2CH2O)2PN(iPr)2, 5-phenyl-1-H-tetrazole, DCM; (h) tBuOOH, −40°C to room temperature; (i) aq ammonia, 70°C; (j) DBU, BSTFA; (k) MeOH, TFA; (l) NaHCO3, Pd(OH)2, H2, tBuOH, H2O.