General, stereoselective synthesis of ethylene isosteres of α- and β-glycosylasparagines

被引:33
作者
Dondoni, A [1 ]
Mariotti, G [1 ]
Marra, A [1 ]
机构
[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
关键词
amino acids; C-glycosides; glycopeptide mimetics; C-glycosylasparagines; sugar acetylenes;
D O I
10.1016/S0040-4039(00)00403-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The coupling of alpha- or beta-D-linked lithium C-glycosyl acetylides with N-Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded alpha- and beta-anomer pairs of C-glycosyl alpha-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3483 / 3487
页数:5
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