A click chemistry approach to the synthesis of 3′-deoxy-2′-substituted carbanucleoside precursors

被引：2

作者：

Ferreira da Costa, Joana ^{[1
]}

Garcia, Marcos D. ^{[1
,2
,3
]}

Garcia-Mera, Xerardo ^{[1
]}

Perez-Castro, Isabel ^{[1
]}

Caamano, Olga ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain

[2] Univ A Coruna, Fac Ciencias, Dept Quim Fundamental, La Coruna, Spain

[3] Univ A Coruna, Fac Ciencias, CICA, La Coruna, Spain

来源：

TETRAHEDRON | 2015年 / 71卷 / 02期

关键词：

Carbanucleosides; Click chemistry; Huisgen's 1,3-dipolar cycloaddition; Aziridines; Haloazides; CARBOCYCLIC NUCLEOSIDES; HIGHLY EFFICIENT; ENANTIOSELECTIVE SYNTHESIS; CYTOSTATIC ACTIVITIES; CYCLIZATION REACTIONS; GUANOSINE ANALOGS; CYCLOBUTANE RING; RIBAVIRIN; AZIRIDINES; CATALYSIS;

D O I：

10.1016/j.tet.2014.11.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein the synthesis of various carbanucleoside precursors by a click chemistry approach, employing cyclopent-3-en-1-ylmethanol 1 as starting material. Using aziridine (+/-)-2 as key intermediate, we describe an efficient procedure for the synthesis of a series of 3'-deoxy-2'-substituted carbanucleoside precursors, namely aminoalcohols of type (+/-)-3. Alternatively, transformation of alcohol 1 into (3-azido-4-halo-1-cyclopentyl)methanols of type (+/-)-4, allows the preparation of 1,2,3-triazole carbanucleoside analogues of types (+/-)-5 and (+/-)-8. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：324 / 331

页数：8

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