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Synlett 2021; 32(20): 2075-2079
DOI: 10.1055/a-1670-2290
DOI: 10.1055/a-1670-2290
letter
A Metal-Free β-Stereoselective Synthesis of 2-Deoxy-C-arylglycosides: Synthesis of 5-Aza Analogues of Aquayamycin
Authors
The project was partially funded by the Natural Science Foundation of Shanghai (11ZR1410400) and by the Large Instruments Open Foundation of East China Normal University (20162015).
Abstract
A convenient protocol for the β-stereoselective synthesis of 2-deoxy-C-arylglycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate a glycosyl acetate to generate a glycosyl iodide intermediate in situ, which is captured by a naphthol; this is followed by a Fries-like O-to-C glycoside rearrangement to afford a β-C-aryl glycoside selectively. The approach is applicable to a wide range of naphthol moieties, and its utility was demonstrated in syntheses of 5-aza analogues of aquayamycin.
Key words
glycosylation - deoxyarylglycosides - glycosyl iodides - metal-free synthesis - aquayamycinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1670-2290.
- Supporting Information (PDF)
Publication History
Received: 21 July 2021
Accepted after revision: 15 October 2021
Accepted Manuscript online:
15 October 2021
Article published online:
11 November 2021
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- 26 Product 3a; Typical Procedure I2 (50.8 mg, 0.2 mmol) was added to a stirred solution of 1a (54.8 mg, 0.2 mmol) and 2-naphthol (2a; 43.2 mg, 0.3 mmol) in anhyd DCE (4 mL) at rt. After 5 min, Et3SiH (9.6 μL, 0.06 mmol) was added. When the reaction was complete (TLC), it was quenched with sat. aq Na2S2O3 (5 mL), and the mixture was extracted with CH2Cl2 (20 mL). The combined organic layers were washed with brine (5 mL), dried (Na2SO4), filtered, and concentrated under vacuum. The crude product was purified by column chromatography (silica gel, PE–EtOAc) to give a yellow syrup; yield: 70.9 mg (99%). [α]25D = +67.0° (c 2.12, CH2Cl2). 1H NMR (500 MHz, CDCl3): δ = 8.61 (s, 1 H), 7.76 (d, J = 8.0 Hz, 1 H), 7.70 (d, J = 8.9 Hz, 1 H), 7.66 (d, J = 8.6 Hz, 1 H), 7.48 (t, J = 7.5 Hz, 1 H), 7.32 (t, J = 7.4 Hz, 1 H), 7.11 (d, J = 8.9 Hz, 1 H), 5.55 (dd, J = 11.9, 1.7 Hz, 1 H), 5.27 (ddd, J = 11.4, 9.6, 5.2 Hz, 1 H), 5.00 (t, J = 9.6 Hz, 1 H), 3.81 (dq, J = 12.3, 6.1 Hz, 1 H), 2.49 (ddd, J = 13.6, 5.1, 1.9 Hz, 1 H), 2.15–2.08 (m, 1 H), 2.12 (s, 3 H), 2.01 (s, 3 H), 1.39 (d, J = 6.2 Hz, 3 H). ESI-MS: m/z [M + Na]+ calcd for C20H22NaO6: 381.13; found: 381.17.