Gustafsson Tomas, Saxin Maria, Kihlberg Jan
Organic Chemistry, Department of Chemistry, Umeå University, SE-901 87 Umeå, Sweden.
J Org Chem. 2003 Mar 21;68(6):2506-9. doi: 10.1021/jo026758d.
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.
已从2,3,4,6-四-O-苄基-D-吡喃半乳糖内酯（1）经14步反应制备出β-D-半乳糖基苏氨酸的C-连接类似物。合成过程中产生了三个手性中心，C-糖苷的异头中心首先通过将格氏试剂加成到1上，随后用三乙基硅烷还原中间体半缩醛而生成。苏氨酸部分的两个手性中心均通过埃文斯手性N-酰基恶唑烷酮烯醇盐的烷基化反应构建。
