Synlett, Table of Contents Synlett 2013; 24(4): 522-526DOI: 10.1055/s-0032-1318196 letter © Georg Thieme Verlag Stuttgart · New York Unexpected Cyclization During the Mitsunobu Reaction of d-Talose Derivatives Huei-Lin Chuang , R. C. Sawant , Shun-Yuan Luo* Recommend Article Abstract Buy Article All articles of this category Abstract A d-talose derivative underwent unexpected cyclization during a Mitsunobu reaction. A plausible pathway for the reaction involves an attack of the nucleophilic azide on the benzyl ring by intramolecular cyclization with loss of the benzyl group. These newly formed, unexpected compounds may be used in the synthesis of derivatives of C-nucleosides. Key words Key wordsMitsunobu reaction - tetrahydroxy-LCB - d-talose - nucleosides - cyclization Full Text References References and Notes 1 Huei-Lin Chuang and R. C. Sawant contributed equally to this work. 2a Mitsunobu O, Yamada M. Bull. Chem. Soc. Jpn. 1967; 40: 2380 2b Mitsunobu O, Yamada M, Mukaiyama T. Bull. 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Tetrahedron Lett. 2003; 44: 5281 13 Procedure for the Synthesis of Compound 19 To a solution of olefin 17 (104 mg, 0.15 mmol) and Ph3P (116 mg, 0.47 mmol) in anhyd THF (1 mL) was stirred at 0 °C. Diisopropyl azodicarboxylate (87 μL, 0.44 mmol) and diphenyl phosphoryl azide (102 μL, 0.44 mmol) were slowly added to the reaction mixture at 0 °C. The reaction mixture was stirred at r.t. overnight. The solvent was evaporated and the colorless oil 19 (57 mg, 0.096 mmol, 64%) was obtained by column chromatography. Analytical Data for Compound 19 1H NMR (400 MHz, CDCl3): δ = 7.71–7.67 (m, 4 H, ArH), 7.45–7.26 (m, 6 H, ArH), 5.63–5.60 (m, 1 H, CH=CH), 5.45–5.40 (m, 1 H, CH=CH), 4.74 (dd, J = 6.4, 3.2 Hz, 1 H, H-3), 4.68–4.64 (m, 1 H, H-1), 4.37 (t, J = 4.8 Hz, 1 H, H-2), 4.10 (td, J = 7.2, 4.0 Hz, 1 H, H-4), 3.77 (d, J = 3.6 Hz, 1 H, H-5), 2.17–2.11 (m, 2 H, CH2), 1.57 (s, 3 H, CH3), 1.40–1.38 (m, 2 H, CH2), 1.35 (s, 3 H, CH3), 1.31–1.26 (m, 16 H, CH2), 1.06 (m, 9 H, CH3), 0.90–0.86 (m, 3 H, CH3). 13C NMR (150 MHz, CDCl3): δ = 135.7 (2 × CH), 135.6 (2 × CH), 134.7 (CH), 133.3 (C), 133.1 (C), 129.71 (CH), 129.66 (CH), 127.72 (CH), 127.69 (2 × CH), 127.65 (2 × CH), 113.8 (C), 85.9 (CH), 84.0 (CH), 82.3 (CH), 80.5 (CH), 64.2 (CH2), 31.9 (CH2), 29.69 (CH2), 29.66 (CH2), 29.64 (CH2), 29.61 (CH2), 29.5 (CH2), 29.4 (CH2), 29.3 (CH2), 28.0 (CH2), 27.6 (CH3), 26.8 (3 × CH3), 25.6 (CH3), 22.7 (CH2), 19.3 (C), 14.1 (CH3). 14 Orsato A, Barbagallo E, Costa B, Olivieri S, De Gioia L, Nicotra F, La Ferla B. 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