A click chemistry approach to the synthesis of 3′-deoxy-2′-substituted carbanucleoside precursors. Issue 2 (14th January 2015)

• Record Type: Journal Article
• Authors: da Costa, Joana Ferreira; García, Marcos D.; García-Mera, Xerardo; Pérez-Castro, Isabel; Caamaño, Olga
• Is Part Of: Tetrahedron. Volume 71:Issue 2(2015)
• Page Start: 324
• Page End: 331
• Publication Date: 2015-01-14
• Subjects: Carbanucleosides -- Click chemistry -- Huisgen's 1, 3-dipolar cycloaddition -- Aziridines -- Haloazides; VBQWNGZINRVGLV-UXIGCNINSA-N -- PVXQCRAZWPSPEP-HSUXUTPPSA-N -- ZQRNNHNNKCDBHM-WOJBJXKFSA-N -- GIKKZKDJWBNCOZ-HSUXUTPPSA-N -- OGCFBDFJPXBFSU-HSUXUTPPSA-N -- VSKKAGDUFVETTG-IVMMDQJWSA-N -- BYIVVPZCLYHLEN-VDHBEHJQSA-N -- TUTPPVDKFOCZLS-OSAQELSMSA-N -- STGIVDNTOBYFRO-RAIGVLPGSA-N -- SFALHPSLJGNLIJ-SAWYMBPVSA-N -- MCNJJYNFZCKSOC-YRGRVCCFSA-N -- WDLUMBXYUBUGDR-UCNVEGJOSA-N -- JSSAEBSXPQCEDZ-MBNYWOFBSA-N -- GLUNBYMYFQZKAE-IACUBPJLSA-N -- CJAQZNRBPIEHPK-RAIGVLPGSA-N -- VPCMIANMYBSGLU-OCCSQVGLSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2014.11.043
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We report herein the synthesis of various carbanucleoside precursors by a click chemistry approach, employing cyclopent-3-en-1-ylmethanol1 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 alcohol1 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 . Graphical abstract: