81936-99-4

Upstream product

• 51515-92-5 2-O-Acetyl-1,6-anhydro-3,5-di-O-benzyl-β-D-glucofuranose 
• 81936-95-0 2-O-Acetyl-1,6-anhydro-3-O-benzyl-β-D-xylo-hexofuranos-5-ulose 
• 81936-93-8 2-O-Acetyl-1,6-anhydro-3-O-benzyl-β-D-glucofuranose 
• 108-24-7 acetic anhydride 
• 81936-98-3 1,6-Anhydro-3-O-benzyl-α-L-idofuranose 

Relevant academic research and scientific papers

1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose

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.