Synthesis of methylene isosteres of α- and β-D-galactopyranosyl-L-serine

被引:36
作者
Dondoni, A [1 ]
Marra, A [1 ]
Massi, A [1 ]
机构
[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
关键词
D O I
10.1039/a800571k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The BF3. Et2O promoted coupling of tetra-O-benzyl-alpha-D-galactopyranosyl trichloroacetimidate with a silyl enol ether carrying an oxazolidine ring leads to the alpha-C-glycosylmethyl ketone (32%, 95% ds) that is converted into the title alpha-C-glycosyl amino acid by carbonyl oxygen removal (Barton-McCombie) and oxidative cleavage (Jones) of the heterocyclic ring, and into the beta-isomer by anomerization and the same two-step sequence.
引用
收藏
页码:1741 / 1742
页数:2
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