A Metal-Free β-Stereoselective Synthesis of 2-Deoxy-C-arylglycosides: Synthesis of 5-Aza Analogues of Aquayamycin

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 - aquayamycin

• References and Notes

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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). 1}H 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.