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

共 50 条

[1] Design and Synthesis of 2′-Deoxy-2′-[(1,2,3)Triazol-1-Yl]Uridines Using Click Chemistry Approach
Kumar, Surender
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2015, 34 (05): : 371 - 378
[2] Synthesis of 4-substituted-1,2,3-triazole carbanucleoside analogues of ribavirin via click chemistry
Perez-Castro, Isabel
Caamano, Olga
Fernandez, Franco
Garcia, Marcos D.
Lopez, Carmen
De Clercq, Erik
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (23) : 3805 - 3813
[3] Synthesis of 2'-deoxy-2'-substituted-4'-thiocytidines
Lloyd, AW
DRUG DISCOVERY TODAY, 1996, 1 (06) : 264 - 264
[4] Synthesis of 3′-Deoxy-3′-difluoromethyluridine and 2′-Deoxy-2′difluoromethyluridine
Marcotte, Stéphane
Gérard, Baudoin
Pannecoucke, Xavier
Feasson, Christian
Quirion, Jean-Charles
Synthesis, 2001, (06) : 929 - 933
[5] Synthesis of 3′-deoxy-3′-difluoromethyluridine and 2′-deoxy-2′-difluoromethyluridine
Marcotte, S
Gérard, B
Pannecoucke, X
Feasson, C
Quirion, JC
SYNTHESIS-STUTTGART, 2001, (06): : 929 - 933
[6] Synthesis of 8-substituted analogues of 2′-deoxy-2′-fluoroadenosine
Maruyama, T
Kozai, S
Manabe, T
Yazima, Y
Satoh, Y
Takaku, H
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (11-12): : 2433 - 2442
[7] SYNTHESIS OF 2'-DEOXY-2'THIO-3'-DEOXY-3'-AMINOURIDINE
SEKIYA, T
UKITA, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1967, 15 (10) : 1503 - +
[8] SYNTHESIS OF 2'-DEOXY-2'-THIO-3'-DEOXY-3'-AMINOURIDINE
SEKIYA, T
UKITA, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1967, 15 (04) : 542 - +
[9] EFFICIENT SYNTHESIS OF 2'-DEOXY-2'-ALPHA-C-SUBSTITUTED NUCLEOSIDES
SCHMIT, C
SYNLETT, 1994, (04) : 238 - 240
[10] SYNTHESIS OF 2'-DEOXY-2'-FLUOROADENOSINE AND OTHER 2'-SUBSTITUTED 2'-DEOXYADENOSINE DERIVATIVES
RANGANATHAN, R
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1976, 172 (SEP3): : 91 - 91

← 1 2 3 4 5 →