6194
P. Pullanikat et al. / Tetrahedron Letters 51 (2010) 6192–6194
ammonium formate, whereas non-reducing sugars were resistant
O
H
ONH4
HCOONH4
to oxidative degradation. We believe that the conditions developed
herein are more practical and useful compared to the previously
known methods due to the efficiency at ambient temperature,
short reaction time, environment friendly solvent, and high
chemoselectivities.
H2O2
H
O
O
H
(HO
H)n
CH2OH
Lower Aldose
Through
NH4OH
rt
OH
H
(HO
H)n-1
CH2OH
Aldose
hydroper-
oxide adduct
OH
Hydroperoxide
adduct
Acknowledgments
(n+1) HCOONH4
The authors would like to acknowledge Joo Ho Lee, Thomas
Mathew, Richard Giles, and Victor Hadi for editing the Letter and
for their valuable suggestions. The authors would like to thank
the Hydrocarbon Research Foundation and the National Institute
of Health (S10 RR025432) for generous financial support.
COONH4
CH2OH
CH2OH
O
CH2OH
H4NO
O
H
H2O2
OH
Lower Aldose
(HO
H)n
O
H
NH4OH
rt
CH2OH
(HO
H)n-1
Through
hydroper-
oxide adduct
OH
CH2OH
Supplementary data
Ketose
Hydroperoxide
adduct
Supplementary data (1H wet 1D NMR’s of all entries in Tables
1–3, reaction mixtures of the compounds in Scheme 2, ammonium
formate, and a mixture of ammonium formate and formic acid.)
associated with this article can be found, in the online version, at
(n+1) HCOONH4
H2O2
COOH
No oxidation or
degradation
product
NH4OH
rt
CH2OH
Glycolic
acid
References and notes
Scheme 1. Possible mechanism for the oxidative degradation of aldose and ketose
to ammonium formate.
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Melezitose
Raffinose
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O
galactose
O
OH
HO
O
OH
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HO
OH
OH
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Sucrose-nonreducing part
Scheme 2. Nonreducing trisaccharides.
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