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Synlett 2018; 29(05): 668-672
DOI: 10.1055/s-0036-1591525
DOI: 10.1055/s-0036-1591525
letter
Substoichiometric FeCl3 Activation of Propargyl Glycosides for the Synthesis of Disaccharides and Glycoconjugates
This project was financially supported by Natural Science Foundation of Shanghai (11ZR1410400), Shanghai college student innovative training program (201510269085) and large instruments Open Foundation of East China Normal University (20151043 & 20162015).Further Information
Publication History
Received: 05 October 2017
Accepted after revision: 03 December 2017
Publication Date:
03 January 2018 (online)
Abstract
Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective, affordable, and green glycosylation procedure.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591525.
- Supporting Information
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- 55 Typical Experimental Procedure Typically, to a mixture of 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside (1a, 0.1 mmol, 58 mg) and methyl 2,3,4-tri-O-benzoyl-α-d-glucopyranoside (2a, 0.05 mmol, 25 mg) in a round-bottom flask (5 mL) under nitrogen atmosphere. The FeCl3 (10 mg, 0.06 mmol) catalyst and anhydrous CH3CN solvent (6 mL) was added to another round-bottom flask. Take the solution of FeCl3(1.5 mL) to the former round-bottom flask, and the reaction was stirred at 60 °C for 15 h. After completion of the reaction (monitored by TLC), the organic phase was condensed under vacuum to get crude product, which was purified by silica gel column chromatography (PE/EtOAc = 6:1) to get 3a in 83% yield. All new compounds were characterized by 1H NMR,13C NMR, and MS. Spectral and analytical data were in good agreement with the desired structures.
- 56 Selected Spectral Data – Compound 3a Colorless oil, α-anomer:1H NMR (500 MHz, CDCl3): δ = 8.00 (dd, J = 8.3, 1.2 Hz, 2 H), 7.97 (dd, J = 8.3, 1.2 Hz, 2 H), 7.91–7.85 (m, 2 H), 7.55–7.49 (m, 2 H), 7.46–7.28 (m, 24 H), 7.22 (m, 1 H), 7.15 (dd, J = 7.6, 1.7 Hz, 2 H), 6.16 (t, J = 9.4 Hz, 1 H), 5.55 (t, J = 9.9 Hz, 1 H), 5.24 (q, J = 3.5 Hz, 2 H), 4.93 (d, J = 11.0 Hz, 1 H), 4.84 (d, J = 11.0 Hz, 1 H), 4.80 (d, J = 11.0 Hz, 1 H), 4.78 (d, J = 12.5 Hz, 1 H), 4.76 (d, J = 3.5 Hz, 1 H), 4.65 (d, J = 12.2 Hz, 1 H), 4.56 (d, J = 12.1 Hz, 1 H), 4.47 (d, J = 11.0 Hz, 1 H), 4.40 (d, J = 12.1 Hz, 1 H), 4.36–4.31 (m, 1 H), 3.98 (t, J = 9.3 Hz, 1 H), 3.90–3.84 (m, 2 H), 3.67–3.62 (m, 2 H), 3.60 (dd, J = 11.0, 2.1 Hz, 1 H), 3.56 (dd, J = 9.7, 3.5 Hz, 1 H), 3.52 (dd, J = 10.7, 1.9 Hz, 1 H), 3.46 (s, 3 H). β-Anomer: 1H NMR (500 MHz, CDCl3): δ = 8.00–7.85 (m, 6 H), 7.52–7.12 (m, 29 H), 6.17 (t, J =9.8 Hz, 1 H), 5.47 (t, J =9.9 Hz, 1 H), 5.25 (dd, J =10.2, 3.6 Hz, 1 H), 5.20 (d, J =3.6 Hz, 1 H), 5.05 (d, J =10.8 Hz, 1 H), 4.91 (d, J =10.9 Hz, 1 H), 4.80 (d, J =10.8 Hz, 1 H), 4.76 (d, J = 10.9 Hz, 1 H), 4.68 (d, J =10.9 Hz, 1 H), 4.53 (d, J =11.5 Hz, 1 H), 4.50 (d, J =11.6 Hz, 1 H), 4.47 (d, J =7.8 Hz, 1 H), 4.43 (d, J =12.2 Hz, 1 H), 4.41–4.34 (m, 1 H), 4.12 (dd, J =10.8, 2.0 Hz, 1 H), 3.81 (dd, J = 10.9, 7.6 Hz, 1 H), 3.66–3.63 (m, 2 H), 3.61 (d, J = 6.0 Hz, 1 H), 3.58 (d, J = 9.1 Hz, 1 H), 3.46–3.43 (m, 2 H), 3.37 (s, 3 H). ESI-MS: m/z calcd for C62H60O14 Na [M + Na+]: 1051.39; found: 1051.25.