Synthesis of a C-glycoside analogue of beta-D-galactosylthreonine.
A C-linked analogue of beta-D-galactosylthreonine has been prepared from 2,3,4,6-tetra-O-benzyl-D-galactopyranolactone (1) in 14 steps. Three stereogenic centers were created during the synthesis, with the anomeric center of the C-glycoside being generated first by addition of a Grignard reagent to 1 and subsequent reduction of the intermediate hemiacetal with triethylsilane. The two stereogenic centers in the threonine moiety were both established by alkylation of Evans' chiral N-acyloxazolidinone enolates.
Gustafsson
Tomas
T
Organic Chemistry, Department of Chemistry, Umeå University, SE-901 87 Umeå, Sweden.
Saxin
Maria
M
Kihlberg
Jan
J
D000478:Alkylation; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism; D013912:Threonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D006027:Glycosides; D007202:Indicators and Reagents; D012821:Silanes; D013912:Threonine; D005690:Galactose