Aryl and Arylmethyl C-Glycosides through Desulfitative Stille and Carbonylative Stille Cross-Coupling of Tinglycals and Sulfonyl Chlorides

Abstract

The palladium-catalyzed cross-coupling of tinglucal and tingalactal derivatives with arenesulfonyl chlorides provides aryl C-glycoside precursors. Desulfitative carbonylative Stille cross-coupling between 1-naphthalenesulfonyl chloride and a tinglucal derivative gives, after stereoselective reduction of the keto moiety and stereoselective oxidative hydroboration, a protected form of 1-[(1S)-2,6-anhydro-l-glycero-d-gulo-heptitol-1-C-yl]naphthalene [β-C-glucopyranoside of (S)-(naphtha-1-yl)methanol]. Benzyl C-glycoside precursors are obtained by desulfitative Stille coupling of phenylmethanesulfonyl chloride with the corresponding protected tinglycals.

sulfonyl chlorides - tinglycals - C-glycosides - cross-coupling - catalysis - palladium

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Catalyst and ligands were bought from Strem Chemical, Inc.

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Data for 20: ¹H NMR (400 MHz, CDCl₃): δ = 8.12 (d, 1 H, J = 8.3 Hz, H_nap), 7.80 (m, 1 H, H_nap), 7.75 (d, 1 H, J = 8.3 Hz, H_nap), 7.51 (d, 1 H, J = 7.1 Hz, H_nap), 7.44 (m, 2 H, H_nap), 7.37 (t, 1 H, J = 7.7 Hz, H_nap), 4.96 (d, 1 H, J = 9.3 Hz, H₁), 4.79 (br s, 1 H, OH), 4.36 (br s, 1 H, OH), 3.93 (t, 1 H, J = 9.0 Hz, H₂), 3.86 (m, 3 H, H₃, H₄, H₆), 3.77 (t, 1 H, J = 9.0 Hz, H₅), 3.61 (m, 1 H, H₆), 3.28 (br s, 1 H, OH), 2.77 (br s, 1 H, OH). ¹³C NMR (100.1 MHz, CDCl₃): δ = 134.8 (C_nap), 133.9 (C_nap), 132.2 (C_nap), 128.7 (C_nap), 128.6 (C_nap), 126.1 (C_nap), 125.6 (C_nap), 125.5 (C_nap), 125.4 (C_nap), 124.5 (C_nap), 80.4 (C₃), 78.9 (C₄), 78.5 (C₁), 74.3 (C₂), 71.2 (C₅), 62.9 (C₆). IR (NaCl): 3384, 2925, 1450, 1085, 780 cm^-1. MS: m/z (%) = 291 (10), 273 (8), 185 (12), 142 (100), 100 (24). HRMS (MALDI-TOF): calcd [C₁₆H₁₈O₅ + Na] 313.1052; found: 313.1059.

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