THE SYNTHESIS OF D-EVALOSE

D-Evalose (1: 6-deoxy-3-C-methyl-D-mannose) was synthesized from methyl 3, 3′-anhydro-4, 6-O-benzylidene-3-C-hydroxymethyl-2-O-methyl-α-D-mannopyranoside (3) through five-step derivations, and the structure was confirmed by the conversion into D-nogaloside (8: methyl 6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-α-D-mannopyranoside)

SYNTHESIS OF METHYL β-D-VIRENOSIDE

Methyl 6-deoxy-3-C-methyl-β-D-gulopyranoside (1: methyl β-D-virenoside) has been synthesized from galactose. The introduction of methyl branching at C-3 position was achieved by the Grignard reaction

Branched-chain Sugars. XXIX. Synthesis of Moenuronic Acid (4-C-Methyl-D-glucuronic Acid)

Moenuronic acid (4-C-methyl-D-glucuronic acid), a branched-chain sugar component of moenomycin A, was synthesized by the introduction of an axial C-methyl group into methyl 2,3-di-O-benzyl-6-O-trityl-α-D-xylo-hexopyranosid-4-ulose by the reaction with methyllithium, followed by deprotection and platinum-catalyzed oxidation of the C-6 position. Stereoselectivities in a few reactions for the introduction of C-methyl group were examined

SYNTHESIS OF METHYL 2,3-DI-O-METHYL-α-D-SIBIROSAMINIDE

Methyl 2,3-di-o-methyl-α-D-sibirosaminide (12; methyl 4,6-dideoxy-3-c-methyl-2,3-di-o-methyl-4-methylamino-α-D-altropyranoside) has been synthesized from methyl 4,6-o-benzylidene-3-c-methyl-2-o-methyl-α-D-altropyranoside (2). The introduction of methylamino group at c-4 position was achieved by hydrogenation of methyl 6-deoxy-3-c-methyl-2,3-di-o-methyl-α-D-arabino-hexopyranosid-4-ulose oxime (8) in the ratio of 2.6:1 (altro:ido) followed by N-formylation and reduction