Synthesis and utility of 2-(benzoyloxyimino)-2-deoxy-alpha-D-lyxo-hexopyranosyl bromide as a novel alpha-D-talosaminide building block.
A novel alpha-D-talosaminyl donor, 2-(benzoyloxyimino)-2-deoxy-alpha-D-lyxo-hexopyranosyl bromide has been synthesized in a total yield of 32% over 6 steps from D-galactose. The utility of the donor was evaluated for the elaboration of alpha-D-TalNAc-(1-->6)-alpha-D-Gal, alpha-D-TalNAc-(1-->6)-alpha-D-Glc, and alpha-D-TalNAc-(1-->3)-L-serine derivatives by a simple 3-step sequence, comprising alpha-selective glycosylation of appropriately protected acceptors of D-galactose, D-glucose, and L-serine, talo-selective hydroboration of the oxyimino function to an amino group, and N-acetylation.
Kaji
E
E
School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
Osa
Y
Y
Takahashi
K
K
Zen
S
S
D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
C098195:3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-lyxo-hexopyranosyl bromide; D006027:Glycosides; D006595:Hexosamines; C098194:N-acetyltalosamine; D009844:Oligosaccharides