. Author manuscript; available in PMC: 2011 May 27.

Published in final edited form as: J Med Chem. 2010 May 27;53(10):4166–4176. doi: 10.1021/jm1001265

Table 1.

Optical Activity and Chiral HPLC Purity of four Diastereoisomers of Compound 4.

Compd	Optical Activity	Optical rotation [α] (C = 0.1 in EtOH)	HPLC Purity (−) : (+)
14	(S, +, S)	−9.7 ± 0.5°	0.49 : 99.51
10	(S, +/−, S)	−29.0 ± 1.0°	49.43 : 50.57
13	(S, −, S)	−49.0 ± 1.0°	99.13 : 0.87
11	(R, −, R)	+17.7 ± 0.5°	99.50 : 0.5
9	(R, +/−, R)	+35.0 ± 0.5°	49.8 : 50.2
12	(R, +, R)	+53.0 ± 1.5°	0.39 : 99.61
4	(RS, +/−, RS)	+1.0 ± 0.5°	48.16 : 51.84
	(R)	+34.2 ± 0.1° ^a*	99 : 1
	(S)	−32.8 ± 0.1° ^b*	99 : 1

^a*

Optical activity [α]22/D + 35.0°, C = 1 in Ethanol, commercially available from Sigma-Aldrich.

^b*

Optical activity [α]22/D − 35.0°, C = 1 in Ethanol, commercially available from Sigma-Aldrich.