2
860
M. K. Mishra et al. / Tetrahedron: Asymmetry 20 (2009) 2854–2860
Table 3
HPLC analysis conditions on a chiral stationary phase for various substrates and products
Column
Mobile phase
Flow rate (mL/min)
Detection wavelength (nm)
Retention times (min)
Chiralpak AD-H
3% 2-propanol in hexane + 0.1% trifluoroacetic acid
0.7
0.5
220
230
(R)-7b: 33.7, (S)-7b: 36.8
(R)-1a: 22.0, (S)-1a: 23.9
(R)-1b: 47.9; (S)-1b: 54.7
5% 2-propanol in hexane + 0.1% trifluoroacetic acid
220
(
R)-9a: 24.7, (S)-9a: 32.8
0
.7
220
20
230
(R)-6b: 14.7, (S)-6b: 16.9
(R)-8b: 30.6, (S)-8b: 34.3
(2S, 3R)-11: 12.7
2
7.5% 2-propanol in hexane
0.5
1.0
(
2R,3S)-11: 13.7
10% 2-propanol in hexane + 0.1% trifluoroacetic acid
254
(S)-4a: 11.2, (R)-4a: 12.7
(S)-4b: 15.5, (R)-4b: 17.5
(R)-9b: 8.0, (S)-9b: 9.5
2
2
20
20
(
R)-10b: 22.8, (S)-10b: 29.6
(2S, 3R)-12: 9.5
2R,3S)-12: 10.6
15% 2-propanol in hexane
0.7
230
(
Chiracel OD
1% 2-propanol in hexane + 0.1% trifluoroacetic acid
0.5
0.5
0.7
230
230
246
(R)-2a: 16.5, (S)-2a: 18.1
(R)-2b: 17.8, (S)-2b: 20.1
(S)-3a: 15.3, (R)-3a: 16.9
(S)-5a: 9.5, (R)-5a: 10.8
(2R,3R)-15: 11.0,
5
1
% 2-propanol in hexane + 0.1% trifluoroacetic acid
0% 2-propanol in hexane + 0.1% trifluoroacetic acid
254
20% 2-propanol in hexane
0.7
230
(
2S,3S)-15: 15.6
(R)-6a: 17.0, (S)-6a: 19.1
R)-10a: 23.6, (S)-10a: 25.2
(R)-7a: 14.0, (S)-7a: 17.1
R)-8a: 23.4, (S)-8a: 27.5
Chiralcel OD-H
3% 2-propanol in hexane + 0.1% trifluoroacetic acid
% 2-propanol in hexane + 0.1% trifluoroacetic acid
1
220
220
(
5
0.7
(
A., 3rd ed.. In The Enzymes; Boyer, P., Ed.; Academic Press: New York,
983; Vol. 16, pp 307–353.
Acknowledgements
1
1
0. (a) Fadnavis, N. W.; Sheelu, G.; Mani Kumar, B.; Bhalerao, M. U.; Deshpande, A.
Biotechnol. Prog. 2003, 19, 557–564; (b) Fadnavis, N. W.; Vedamyee Devi, A.;
Swarnalatha, L. Tetrahedron: Asymmetry 2008, 19, 1139–1144; (c) Fadnavis, N.
W.; Radhika, K. R.; Madhuri, K. V. Tetrahedron: Asymmetry 2004, 15, 549–553;
We are thankful to CSIR, New Delhi and DST, New Delhi, for
financial assistance and Novozymes, Denmark, for gift of Lecitase
Ultra.
Ò
(
d) Fadnavis, N. W.; Deshpande, A. Curr. Org. Chem. 2002, 6, 393–410; (e)
Fadnavis, N. W.; Luke Babu, R.; Sheelu, G.; Deshpande, A. Tetrahedron:
Asymmetry 2001, 12, 1695–1699; (f) Fadnavis, N. W.; Luke Babu, R.; Sheelu,
G.; Deshpande, A. Tetrahedron: Asymmetry 2000, 11, 3303–3309.
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