Methyl ether as a protective group. Synthesis of amino-cyclitols

Article abstract of DOI:10.1016/0008-6215(91)84073-N

The O-methyl(protective) group has proved to be advantageous in a stereoselective synthesis of inosamines and inosdiamines, but the final complete removal remained a challenge. This paper describes a modified work-up that was developed to avoid the usual treatment with active carbon by reduction of all remaining Cr(VI) with sodium oxalate and neutralization of the mixture with sodium carbonate prior to extraction with chloroform. The yield achieved in this way now justify the choice of the O-methyl protective group in multi-step synthesis.