Beilstein J. Org. Chem.2016,12, 328–333, doi:10.3762/bjoc.12.35
anomerization reaction from an easily prepared β-aminoglycoside through endocyclic cleavage.
Keywords: anomerization; aminoglycoside; endocycliccleavagereaction; inositol; mycothiol; Introduction
Tuberculosis is an infectious disease and has had a high death rate over the past few decades [1][2][3][4]. The
pyranosides with N-acetyl 2,3-trans-carbamate groups exhibited complete anomerization from β-glycoside to α-glycoside in the presence of a weak Lewis acid through an endocycliccleavagereaction [29][30][31][32][33]. We showed evidence of the endocycliccleavagereaction by trapping linear cations through
Beilstein J. Org. Chem.2012,8, 456–460, doi:10.3762/bjoc.8.52
hand, the corresponding α-isomer of disaccharide 8α was obtained as a major product together with the anomerized donor 9 when the reaction was performed at 0 °C in the absence of DTBMP (Table 3, entry 4). These anomerizations may be caused by the endocycliccleavagereaction [22][23][24], which is
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Graphical Abstract
Scheme 1:
Electrochemical conversion of thioglycosides to glycosyl triflates.