3- and 4-Uloses Derived from N-Acetyl-d-glucosamine: A Unique Pair of Complementary Organocatalysts
ulose 5 (33.0 mg, 0.07 mmol, 15 mol%) was added. The rest
of the oxone buffer was added in small portions over 5 h.
The mixture was stirred until cinnamyl acetate was con-
sumed or no further change in TLC was seen. The resulting
mixture was diluted with half-saturated brine (15 mL) and
extracted with ethyl acetate (4ꢄ20 mL). The combined or-
ganic phases were dried (MgSO4) and the filtrate was evapo-
rated. The crude product was purified over silica gel (4 g,
column 0.5 cmꢄ12 cm; eluent petrol ether:ethyl acetate
90:10) to afford the epoxide as a colourless liquid; yield:
81.0 mg (0.42 mmol, 85%); [a]2D0: À47 (c 1.00, CH2Cl2; er
81:19), lit.:[33] [a]D22: À50 (c 0.5, CHCl3; 89% ee); GC
(bondex a, 0.4 bar H2, 408C for 1 min, then 2.58CminÀ1 up
to 2008C): tR =38.33 min (major enantiomer), tR =39.18 min
(minor enantiomer); NMR and IR data, see lit.[24]
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Acknowledgements
We would like to thank the Landesgraduiertenfçrderung
Baden-Wꢀrttemberg for a scholarship to C. Schçberl and
Prof. Dr. J. Senn-Bilfinger (Altana Pharma, now Nycomed)
for financial support.
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