Z. Xi et al. / Tetrahedron Letters 47 (2006) 3337–3339
3339
Supplementary data
Supplementary data contains experimental details of the
syntheses, crystal structural data, biological data and
NMR spectra of all the four diastereoisomers. Supple-
mentary data associated with this article can be found,
References and notes
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Figure 2. X-ray analysis of 7c showing the Rc ꢀ Ss configuration.
of the chiral carbon is small, so the CD spectra of the dia-
stereoisomers are nearly mirror images. The CD spectra
show that compounds 1b and 1d have a negative sign of
the Cotton effect at 220–240 nm, it correlates with (R)-
configuration, while compounds 1a and 1c showing a po-
sitive sign have (S)-configuration. The assignment is also
in accordance with the conclusion obtained by analysis of
single-crystal X-ray diffraction of compound 7c (Fig. 2).11
´ˇ
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All the four diastereoisomers of S-oxo-[(methylthio)-
methyl]cysteinol were tested against six bacteria includ-
ing Fusarium oxysporum f. sp. cucumerinum Owen, and
Botrytis cinerea, Fulvia fulva, Sclerotinia sclerotiorum
de Bary, Phytophthora capsici, Botryosphaeria berengeri-
ama. All the four compounds show low to moderate
biological activities against certain bacteria at a concen-
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In summary, we have reported herein a convenient route
to prepare two diastereoisomers (1a, 1b) of S-oxo-
[(methylthio)-methyl]cysteinol on a large scale from
the cheap L-serine as the starting material, with accept-
able overall yield. All the four diastereoisomers (1a–d)
can now be obtained conveniently in large quantity.
All the four compounds were tested against certain bac-
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pounds and their biological activities will be reported
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11. CCDC No. 298255 contains the supplementary crystallo-
graphic data for compound 7c. These data can be obtained
or by emailing data_request@ccdc.cam.ac.uk, or by con-
tacting The Cambridge Crystallographic Data Centre, 12,
Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223
336033.
Acknowledgements
We thank NSFC (20272029, 20432010), NSF of Tianjin
(013616311), MOST (2003CB114400), and the Ministry
of Education of China for financial support.