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. Author manuscript; available in PMC: 2020 Dec 21.
Published in final edited form as: Nucleosides Nucleotides Nucleic Acids. 2011 Apr;30(4):264–270. doi: 10.1080/15257770.2011.580291

SCHEME 1.

SCHEME 1

Reagents and conditions: (i) sodium ascorbate, CuSO4, alkyne, tert-Butanol/H2O; (ii) a) MsCl, Et3N, CH2Cl2, 0°C to room temperature, b) NaN3, DMF; (iii) a) 2,4,6-Triisopropylbenzenesulfonyl chloride, DMAP, Et3N, CH2Cl2, b) NH4OH; (iv) NH3/MeOH, 3°C for benzoyl group; TBAF/THF for silyl group; (v) a) BSA, 3-(trimethylsilyl)propargyl alcohol, toluene, 110°C, b) 48% HF(aq), 26% for two steps; (vi) a) MsCl, pyridine, room temperature, 2 hours, b) NaN3, DMF, 85°C, 3 hours, c) NH3/CH3OH, 49%.