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Synthesis 2007(17): 2621-2626  
DOI: 10.1055/s-2007-983827
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclopenta[d]pyridazinediol Precursors of Carbanucleosides

Isabel Pérez-Castroa, Olga Caamaño*a, Marcos D. Garcíaa, Generosa Gómez*b, Franco Fernándeza, Joana Ferreiraa, Carmen Lópeza
a Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)584912; e-Mail: qoolga@usc.es;
b Departamento de Química Orgánica, Facultade de Química, Lagoas-Marcosende, Universidade de Vigo, 36200 Vigo, Spain
Fax: +34(986)813663; e-Mail: ggomez@uvigo.es;
Further Information

Publication History

Received 20 March 2007
Publication Date:
30 July 2007 (online)

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Abstract

The hemiprotected diols 7 and 8, which are prospective precursors of carbanucleosides of this family, were prepared from the mesylates of the corresponding higher homologues by elimination of the mesyloxy group using 1,8-diazabicyclo[5.4.0]undec-7-ene followed by ozonolysis and reduction of the ozonide with sodium borohydride.

Key words

cyclopenta[d]pyridazines - silyl ethers - diols - ozonolysis - Mitsunobu reaction

10

The crystallographic data of cis-7 have been deposited with the Cambridge Crystallographic Data Centre (CCDC) with number 630734. Empirical formula: C26H32N2O2Si; formula weight: 432.63; crystal size: 0.51 × 0.33 × 0.06; crystal colour, habit: colourless, prismatic; crystal system: monoclinic; lattice type: plate; lattice parameters: a = 6.309 (5) Å, b = 12.889 (5) Å, c = 15.172 (5) Å, α = 90 (5)°, β = 96.818 (5)°, γ = 90 (5)°, V = 1225 0(12) Å3; space group: P21; Z = 2; D calcd = 1.173 Mg/m3; F(000) = 464; R1 = 0.0702, wR2 = 0.1624. Diffractometer: Smart-1000 BRUKER. These data can be obtained free of charge from the CCDC via www.ccdc.ac.uk/data_request/cif.