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DOI: 10.1055/a-2357-7505
One-Pot Assembly of Octasaccharide Motif from Cranberry Arabinoxyloglucan Oligosaccharides
The financial support from National Natural Science Foundations of China (22322110), the Young Talents Project of High-level Talent Introduction Program of Yunnan Province, and the Yunnan Province Science and Technology Department (202305AH340005) is greatly acknowledged.
Abstract
Chemical synthesis of octasaccharide motif from cranberry arabinoxyloglucan oligosaccharides with antiadhesion activities has been achieved for the first time. Synthetic approach highlights the following features: 1) stereoselective constructions of 1,2-cis-Xyl bonds via the combination of reagent modulation and remote participation; 2) modular [1+3+1+3] orthogonal one-pot assembly of the target octasaccharide on the basis of glycosyl ortho-(1-phenylvinyl)benzoate, which avoids the issues such as aglycone transfer associated with one-pot glycosylation based on thioglycosides.
Key words
cranberry - arabinoxyloglucan - chemical synthesis - 1,2-cis-xylosylation - one-pot glycosylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2357-7505.
- Supporting Information
Publikationsverlauf
Eingereicht: 13. Juni 2024
Angenommen nach Revision: 30. Juni 2024
Accepted Manuscript online:
30. Juni 2024
Artikel online veröffentlicht:
17. Juli 2024
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- 18 Procedure for Four-Component [1+3+1+3] Orthogonal One-Pot Synthesis of Octasaccharide 13 A suspension of glucosyl PTFAI 2 (56.0 mg, 0.07 mmol), glucosyl ABz acceptor 3 (79.8 mg, 0.07 mmol), and activated 4 Å MS (250 mg) in dry DCM (0.5 mL) was stirred at room temperature for 15 min under N2 and was then cooled to 0 °C. A solution of HOTf in DCM (0.2 mL, 0.06 M) was slowly added to the mixture. After being stirred at 0 °C for another 2 h, the reaction mixture was warmed up to room temperature, to which glucosyl PVB acceptor 4 (36.7 mg, 0.06 mmol) in DCM (0.5 mL) and freshly prepared solution of Ph3PAuOTf (1.0 mL, 0.012 M) were added successively. After being stirred for another 3 h, the reaction mixture was cooled to 0 °C, then the solution of acceptor 5 (70.7 mg, 0.05 mmol) in DCM (0.6 mL), NIS (18.5 mg, 0.08 mmol), and a solution of HOTf in DCM (0.2 mL, 0.08 M) were successively added. The resulting mixture was stirred at 0 °C to room temperature for another 4 h, then was quenched with Et3N (0.5 mL) and filtered. The filtrates were concentrated under vacuum to give a residue, which was purified by flash column chromatography (PE/EtOAc = 5/1 to 3/1) to afford octasaccharide 13 (112.1 mg, 64% for one pot) as a white foam. [α]D 21 +25.28 (c 0.11, CHCl3). 1H NMR (800 MHz, CDCl3): δ = 8.18 (d, J = 7.2 Hz, 2 H, Ar), 8.03 (d, J = 8.0 Hz, 2 H, Ar), 8.01 (d, J = 8.0 Hz, 2 H, Ar), 7.98–7.97 (m, 4 H, Ar), 7.91 (d, J = 7.2 Hz, 2 H, Ar), 7.89 (d, J = 10.0 Hz, 2 H, Ar), 7.86–7.83 (m, 10 H, Ar), 7.79 (d, J = 7.2 Hz, 2 H, Ar), 7.62–7.59 (m, 3 H, Ar), 7.55–7.51 (m, 6 H, Ar), 7.48–7.45 (m, 3 H, Ar), 7.43–7.39 (m, 10 H, Ar), 7.37–7.36 (m, 4 H, Ar), 7.34–7.28 (m, 24 H, Ar), 7.26–7.24 (m, 7 H, Ar), 7.22–7.18 (m, 9 H, Ar), 7.16–7.14 (m, 5 H, Ar), 7.11–7.07 (m, 8 H, Ar), 7.00–6.98 (m, 1 H, Ar), 6.91–6.89 (m, 5 H, Ar), 6.87–6.85 (m, 2 H, Ar), 6.76–6.75 (m, 2 H, Ar), 6.15 (t, J = 9.6 Hz, 1 H), 5.84–5.79 (m, 3 H), 5.71 (t, J = 9.6 Hz, 1 H), 5.50 (s, 1 H), 5.46 (d, J = 5.6 Hz, 1 H), 5.44 (d, J = 4.8 Hz, 1 H), 5.41 (d, J = 8.0 Hz, 1 H), 5.38 (t, J = 8.8 Hz, 1 H), 5.32 (d, J = 8.8 Hz, 1 H), 5.20 (t, J = 8.8 Hz, 1 H), 5.14–5.11 (m, 3 H), 5.04–5.00 (m, 3 H), 4.86 (d, J = 12.0 Hz, 1 H), 4.78–4.73 (m, 2 H), 4.70 (d, J = 12.0 Hz, 1 H), 4.68–4.64 (m, 2 H), 4.63–4.61 (m, 2 H), 4.56–4.52 (m, 3 H), 4.50–4.49 (m, 2 H), 4.46–4.43 (m, 2 H), 4.37–4.32 (m, 4 H), 4.31–4.29 (m, 1 H), 4.20–4.18 (m, 2 H), 4.13 (d, J = 4.8 Hz, 1 H), 3.99 (d, J = 12.0 Hz, 1 H), 3.87–3.84 (m, 3 H), 3.81–3.74 (m, 4 H), 3.73–3.70 (m, 2 H), 3.66–3.63 (m, 3 H), 3.61–3.58 (m, 2 H), 3.57–3.54 (m, 3 H), 3.49 (d, J = 9.6 Hz, 1 H), 3.39 (t, J = 8.8 Hz, 1 H), 3.28–3.17 (m, 3 H), 2.95–2.82 (m, 2 H), 1.28–1.17 (m, 4 H), 0.97–0.92 (m, 3 H, CH2). 13C NMR (151 MHz, CDCl3): δ = 166.07, 166.04, 165.58, 165.56, 165.50, 165.32, 165.15, 165.12, 164.97, 164.92, 164.82, 164.49, 138.42, 138.31, 138.23, 138.09, 137.95, 137.83, 136.89, 134.14, 133.49, 133.36, 133.24, 133.20, 133.15, 133.09, 133.04, 132.98, 132.87, 132.78, 130.16, 130.12, 130.02, 129.99, 129.93, 129.83, 129.80, 129.75, 129.73, 129.66, 129.64, 129.56, 129.45, 129.08, 129.05, 128.96, 128.74, 128.62, 128.56, 128.53, 128.47, 128.44, 128.39, 128.35, 128.33, 128.29, 128.28, 128.24, 128.20, 128.17, 128.13, 127.95, 127.92, 127.88, 127.83, 127.81, 127.76, 127.70, 127.61, 127.47, 127.14, 127.10, 127.06, 127.01, 126.69, 103.08, 102.93, 101.07, 100.91, 100.76, 100.47, 96.20, 95.83, 82.63, 82.59, 80.98, 80.85, 80.48, 79.52, 78.60, 78.24, 77.49, 76.35, 75.38, 75.28, 75.16, 74.93, 74.80, 74.40, 74.13, 73.79, 73.53, 73.46, 73.37, 73.32, 73.27, 73.21, 72.90, 72.57, 72.30, 72.08, 72.02, 69.63, 67.75, 67.42, 66.98, 63.08, 62.90, 60.33, 59.67, 53.49, 50.44, 50.13, 47.13, 46.11, 31.97, 29.74, 29.70, 29.41, 28.99, 28.84, 27.59, 27.28, 23.03, 22.90, 22.74. MS (Maldi-TOF): m/z calcd for C211H193NO54Na [M + Na]+: 3627.2279; found: 3627.2275.
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