. Author manuscript; available in PMC: 2011 Jan 15.

Published in final edited form as: Bioorg Med Chem. 2009 Nov 27;18(2):809–821. doi: 10.1016/j.bmc.2009.11.046

Table 2.

Click chemistry routes to qCD derivatization

Entry	CD	Ligand	Reaction condition	Product
10^g	1		CuSO₄–5H₂O, NaN₃ sodium ascorbate	EE₂ recovered
11^h	17		CuSO₄–5H₂O, NaN₃ sodium ascorbate	22
12ⁱ	2	7 equiv	CuI, DIEA	7Eqcd,23
13ⁱ	18	1 equiv	CuI, DIEA	1Eqcd,24
14^j			Dimethylsulfate, NaN₃CuSO₄–5H₂O, sodium ascorbate	qE₂,25
15^k	7EqCD,23	NHS–rhodamine
15^k	7EqCD,23	Rhodamine–perchlorate
16ⁱ	2		CuI, DIEA	26
17^k	26	NHS–rhodamine
17^k	26	Rhodamine–perchlorate

DMF/H₂O (3:1), 60 °C, 4 d.

ⁱ

DMF/MeOH, rt, 1 d.

t-BuOH/H₂O (3:1), rt, 1 d.

DMAP/DMF, EDC–HCl/0 °C.