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Synlett 2015; 26(12): 1683-1686
DOI: 10.1055/s-0034-1379929
DOI: 10.1055/s-0034-1379929
letter
Gold- and Silver-Catalyzed Glycosylation with Pyranone Glycosyl Donors: An Efficient and Diastereoselective Synthesis of α-Anomers
Authors
Further Information
Publication History
Received: 19 January 2015
Accepted after revision: 04 May 2015
Publication Date:
25 June 2015 (online)
Abstract
A mild, efficient and diastereoselective gold- and silver-catalyzed O-glycosylation with pyranone glycosyl donors is described. The reactions led to the formation of α-anomers in up to 91% yield with good diastereoselectivities.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379929.
- Supporting Information (PDF) (opens in new window)
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- 8 General Procedure for Gold- and Silver-Catalyzed Glycosylation: To a solution of glycosyl donor l-3 (0.40 mmol) and the appropriate alcohol (0.80 mmol) in anhyd THF (2.0 mL) was added AuCl3 or AgSbF6 (0.020 mmol) at –20 °C under nitrogen atmosphere. The mixture was stirred at –20 °C for 30 min. After removal of the solvent under reduced pressure, the residue was then purified by flash column chromatography on silica gel using an appropriate eluent to give the desired glycoside. α-l-5a: colorless oil; [α]D 21 +21.5 (c = 0.5, CH2Cl2). 1H NMR (400 MHz, CDCl3): δ = 6.80 (dd, J = 10.2, 3.5 Hz, 1 H), 6.05 (d, J = 10.2 Hz, 1 H), 5.33 (d, J = 3.5 Hz, 1 H), 4.59 (t, J = 6.8 Hz, 1 H), 3.64–3.72 (m, 1 H), 1.95–1.98 (m, 1 H), 1.72–1.88 (m, 3 H), 1.46–1.68 (m, 7 H), 0.94–1.38 (m, 20 H), 1.37 (d, J = 6.8 Hz, 3 H), 0.89 (d, J = 6.4 Hz, 3 H), 0.87 (d, J = 1.6 Hz, 3 H), 0.85 (d, J = 1.6 Hz, 3 H), 0.80 (s, 3 H), 0.64 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 197.29, 144.17, 127.20, 91.36, 77.89, 70.28, 56.48, 56.31, 54.38, 44.84, 42.61, 40.04, 39.53, 37.11, 36.19, 35.79, 35.62, 35.50, 34.54, 32.08, 29.34, 28.85, 28.25, 28.01, 24.22, 23.84, 22.81, 22.56, 21.25, 18.68, 15.27, 12.25, 12.08. ESI-MS: m/z = 499.2 [M+ + H]. α-l-5g: white solid; mp 126–127 °C; [α]D 21 +105.3 (c = 0.5, CH2Cl2). 1H NMR (400 MHz, CDCl3): δ = 6.82 (dd, J = 10.2, 3.5 Hz, 1 H), 6.07 (d, J = 10.2 Hz, 1 H), 5.28 (d, J = 3.5 Hz, 1 H), 4.79–4.86 (m, 2 H), 4.08–4.12 (m, 2 H), 3.64–3.68 (m, 1 H), 3.52–3.55 (m, 1 H), 3.36 (s, 3 H), 1.57 (s, 3 H), 1.37 (d, J = 6.7 Hz, 3 H), 1.34 (s, 3 H), 1.30 (d, J = 6.3 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 197.62, 142.75, 127.51, 109.25, 98.04, 93.28, 80.21, 77.13, 76.15, 70.72, 64.75, 54.90, 28.15, 26.38, 17.48, 15.21. ESI–MS: m/z = 329.1 [M+ + H].