Heterocyclic amino sugar derivatives. Part VII. Synthesis of 2-deoxy-2-methylamino-d-gulose and of its 4-methyl 4,6-dimethyl ethers

Article abstract of DOI:10.1016/S0008-6215(00)86187-X

Benzyl 2-deoxy-α-d-gulopyranosido[2,3:4′,5′]-2′-oxazolidinone (10) was synthesized from benzyl 3-O-acetyl-2-[(benzyloxycarbonyl)amino]-2-deoxy-α-d-glucopyranoside (1) via the 4-O-methylsulfonyl-6-O-trityl derivative and 3,4-anhydro-α-d-galactopyranoside derivatives. Compound 10 and its 6-O-trityl and 4,6-O-benzylidene derivatives were permethylated with methyl iodide-barium oxide in N,N-dimethylformamide, the protective groups split off, and the resulting compounds acetylated to give the benzyl glycosides as well characterized, stable compounds that could be hydrolysed to give the title compounds.