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DOI: 10.1055/s-2004-825587
Aryl and Arylmethyl C-Glycosides through Desulfitative Stille and Carbonylative Stille Cross-Coupling of Tinglycals and Sulfonyl Chlorides
Publication History
Publication Date:
10 May 2004 (online)
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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.
Key words
sulfonyl chlorides - tinglycals - C-glycosides - cross-coupling - catalysis - palladium
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References
Catalyst and ligands were bought from Strem Chemical, Inc.
14Data for 20: 1H NMR (400 MHz, CDCl3): δ = 8.12 (d, 1 H, J = 8.3 Hz, Hnap), 7.80 (m, 1 H, Hnap), 7.75 (d, 1 H, J = 8.3 Hz, Hnap), 7.51 (d, 1 H, J = 7.1 Hz, Hnap), 7.44 (m, 2 H, Hnap), 7.37 (t, 1 H, J = 7.7 Hz, Hnap), 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 (Cnap), 133.9 (Cnap), 132.2 (Cnap), 128.7 (Cnap), 128.6 (Cnap), 126.1 (Cnap), 125.6 (Cnap), 125.5 (Cnap), 125.4 (Cnap), 124.5 (Cnap), 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.