A serendipitous discovery of a new C-furanosyl glycine synthesis via thiazole-based aminohomologation of hexopyranoses

被引：7

作者：

Dondoni, Alessandro ^{[1
]}

Massi, Alessandro ^{[1
]}

Nuzzi, Andrea ^{[1
]}

机构：

[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

SYNLETT | 2007年 / 02期

关键词：

amino acids; cyclization; glycopeptides; glycosides; ring closure;

D O I：

10.1055/s-2007-967993

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring closure via microwave-assisted intramolecular OMs displacement by a gamma-OBn group (O-nucleophilic attack) in protected polyhydroxylated N-Boc-thiazolylalkyl amines afforded C-furanosides (37-81%) featuring a chiral thiazolylmethyl amino side chain, which, upon thiazole to carboxylate (through aldehyde) transformation, furnished enantiopure C-furanosyl glycines.

引用

页码：303 / 307

页数：5

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