A highly efficient method for the preparation of phosphinic pseudodipeptidic blocks suitably protected for solid-phase peptide synthesis

被引：26

作者：

Georgiadis, D ^{[1
]}

Matziari, M ^{[1
]}

Yiotakis, A ^{[1
]}

机构：

[1] Univ Athens, Dept Chem, Organ Chem Lab, Athens 15771, Greece

来源：

TETRAHEDRON | 2001年 / 57卷 / 16期

关键词：

phosphinic peptides; zinc metalloprotease inhibitors; Michael addition;

D O I：

10.1016/S0040-4020(01)00221-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Building blocks of the general type FmocXaa Psi {PO(OAd)CH2} YaaOH suitable for solid-phase synthesis of phosphinic peptides have been prepared using a new synthetic strategy based on mild and high-yielding reactions. The key reaction of this method is the Michael addition of activated Fmoc protected silyl aminophosphonites to benzyl acrylates at room temperature. As compared to our previous work, this method consists of less synthetic steps and doubles the overall yield, thus providing a convenient route to phosphinic synthons suitable for the solid-phase preparation of inhibitors of various metalloproteases. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3471 / 3478

页数：8

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