Synthesis of a C-Glycoside Analogue of β-d-Galactosylthreonine
- 25 February 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (6), 2506-2509
- https://doi.org/10.1021/jo026758d
Abstract
A C-linked analogue of β-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.Keywords
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