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. 2013 Dec 6;15(1):57–67. doi: 10.1002/cbic.201300583

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copy; 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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Scheme 2 — Synthesis of FAM-InsP₅ (5). a) Benzoic anhydride, pyridine, DMAP, 0 °C to RT, 84 %; b) NaH, BrCH₂CN, CH₃CN, −30 °C to RT, 85 %; c) i: LiAlH₄, THF, 0 °C; ii: ethyl trifluoroacetate, THF, 66 %; d) i: TFA, CH₂Cl₂, H₂O; ii: (BnO)₂PNPrⁱ₂, 5-phenyltetrazole, CH₂Cl₂; iii: mCPBA, CH₂Cl₂, −78 °C to RT, 88 %; e) i: Pd(OH)₂/C, MeOH, H₂O, H₂, 1 atm; ii: DIPEA, H₂O, 60 °C; quantitative; f) i: 5-carboxyfluorescein succinimidyl ester, propan-2-ol, DIPEA, 60 °C; ii: Q Sepharose Fast Flow, eluting with aqueous 0 to 2.0 m TEAB; iii: LichroPrep RP-18, eluting with 0 to 30 % CH₃CN in aqueous 0.05 m TEAB, 79 %. Bn, benzyl; Bz, benzoyl; TEAB, triethylammonium bicarbonate.