Stereoselective synthesis of 2,3-unsaturated-O-Glycosides promoted by TeBr4

Journal of the Brazilian Chemical Society

Volumn 21, Issue 11, 2010, Pages 2169-2172

  Freitas, Juliano C R ^a   Freitas, João R De ^b   Menezes, Paulo H ^a  

^a DEPARTAMENTO DE QUÍMICA FUNDAMENTAL   (Brazil)

^b UNIVERSIDADE FEDERAL RURAL DE PERNAMBUCO   (Brazil)

Author keywords

2,3 unsaturated O glycosides; O glycosylation; Tellurium tetrabromide

Indexed keywords

EID: 78649597061     PISSN: 01035053     EISSN: 16784790     Source Type: Journal    
DOI: 10.1590/S0103-50532010001100020     Document Type: Article

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42. Representative procedure for the synthesis of prop-2-ynyl-4,6-di-O- acetyl-2,3-dideoxy- α-D-erythro-hex-2-enopyranoside (2a): To a 25 mL round bottomed flask containing a solution of glucal 1 (272 mg, 1.0 mmol) and the appropriate alcohol (1.2 mmol) in dichloromethane (10 mL) at 0 oC was added TeBr4 (Aldrich) (22.4 mg, 5 mol%). The ice bath was removed and the mixture was stirred for the time indicated on Table 2 (or refluxed for the time indicated on Table 3). Brine (5.0 mL) was then added and themixture was stirred until the yellow color disappear. The mixture was extracted with EtOAc (210.0 mL) and the organic phase dried over MgSO4. The solvents were removed under reduced pressure followed by purification by flash chromatography column [hexanes:EtOAc (95:5)] to yield 246 mg (92%) of the title compound as a white solid. mp: 58-59 °C (lit.24 59 °C). 1H NMR (300 MHz, CDCl3): δ 2.07 (s, 3H, -OCOCH3), 2.09 (s, 3H, -OCOCH3), 2.45 (t, J 2,4 Hz, -C≡CH), 4.04-4.10 (m, 1H, H-5), 4.20 (dd, J 11.2 and 5.1 Hz, 2H, Ha-6, Hb-6), 4.29 (d, J 2,4 Hz, -CH2C≡C), 5.22 (br s, 1H, H-1), 5.30-5.34 (m, 1H, H-4), 5.80-5.85 (m, 1H, H-2), 5.91 (br d, J 10,2 Hz, 1H, H-3); 13C NMR (75 MHz, CDCl3): δ 170.7, 170.2, 129.7, 127.1, 92.7, 79.0, 74.8, 67.1, 65.0, 62.7, 55.0, 20.9, 20.7; LMRS (EI) m/z: 268(1), 213(9), 166(23), 153(16), 124(99), 111(25), 95(9), 85(69), 81(11), 67(5), 57(12), 55(10), 43(100).The spectroscopic data of all synthesized compounds match with the reported values: 2f, 2g;24 2b, 2c, 2e, 2i;13 2d, 2h;25 2j, 2m; 2l,26 and 2n.4