A concise C-glycosyl amino acid synthesis by alkenyl C-glycoside-vinyloxazolidine cross-metathesis.: Synthesis of glycosyl serine, asparagine and hydroxynorvaline isosteres

被引:48
作者
Dondoni, A [1 ]
Giovannini, PP [1 ]
Marra, A [1 ]
机构
[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 19期
关键词
D O I
10.1039/b106029p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent synthesis has been developed to afford C-linked glycosyl amino acids by cross-metathesis of vinyl, allyl, and butenyl C-glycosides with N-Boc-vinyloxazolidine using the Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylideneruthenium carbene. the method has been employed to introduce through an alpha -linkage, an alpha -aminopentanoic acid chain,at the anomeric carbon of beta -D-C-gentiobiose to give a totally artificial glycosyl alpha -amino acid of a disaccharide. This compound represents the isostere of the alpha -linked glycosylasparagine moiety of the natural glycopeptide nephritogeno side.
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页码:2380 / 2388
页数:9
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