31880-34-9Relevant articles and documents
1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose
Koell, Peter,John, Hans-Georg,Schulz, Juergen
, p. 613 - 625 (2007/10/02)
The title compound 13 is prepared on different routes from suitable benzyl derivatives with gluco-configuration.Preparations use the susceptibility of axial 5-O-benzyl groups in this compounds to selective hydrogenolysis, thus allowing subsequent inversion of configuration in this position from D-gluco to L-ido by an oxidation/reduction sequence.Only 0.08percent of 13 are found in the equilibrium mixture of idose in acidic medium.It is shown with 4-C-methyltalose as example, that the amount of 1,6-anhydrofuranoses in these equilibria rises significantly by changing the hydroxy groups in 4-position from secondary to tertiary ones.