Total asymmetric synthesis of long-chain, branched carbohydrates and of an Aza-C-disaccharide

Article abstract of DOI:10.1016/0040-4039(96)00189-X

Michael addition of (-)-(1S,5R,6R,7S)-6,7-bis(methoxymethoxy)-2,8-dioxabicyclo[3.2.1]octan -3-one lithium enolate to (+)-(1R,4S,5S,6S)-5-benzeneselenyl-6-chloro-3-methylidene-7-oxabicyclo [2.2.1]heptan-2-one gives a single adduct with high stereoselectivity. It was converted into a derivative of β-D-(1 ← 3)-C-linked 1,5-dideoxy-1,5-imino-lyxopyranoside of α-D-mannofuranurono-6,1-lactone and other long-chain, branched sugars.