8648
K. S. Bisht et al. / Tetrahedron Letters 47 (2006) 8645–8649
upfield shift in the resonance position of C-500 is consis-
tent with the c-effect that is caused by the attachment of
the acyl groups at the C-600 hydroxyl. No significant shift
in the resonance position of the other carbons in 1, in
comparison to those in 1b, were found. These observa-
tions unequivocally established the formation of lactone
ring at C-600 position and the structure of the compound
was established as 1. The regioselectivity of the lipase is
remarkable as only the C-60 hydroxyl, which is in
competition with six other hydroxyl groups (one primary
(C-60) and five secondary), was involved in the macro-
lactone formation exclusively.
Supplementary data
The detailed experimental procedures and NMR spectra
for compounds 1b, 2b, 1, and 2 are provided. Supple-
mentary data associated with this article can be
References and notes
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In compound 2, the DEPT 13C NMR did not show the
methyl ester resonance which was observed in 2b at
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bonyl resonance at 176 ppm suggested a macrolactone
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)
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3. Conclusion
In summary we have demonstrated the highly regioselec-
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best of our knowledge, is the first report of well-defined
glycolipid analogs synthesis from maltose and melibiose,
two readily available disaccharides. Presently we are
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Financial support for this work from the American Can-
cer Society, the Herman Frasch Foundation, and the
American Lung Association is greatly appreciated. We
wish to thank Dr Edwin Rivera for his help with acqui-
sition of the NMR data.