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DOI: 10.1055/s-2006-926231
Synthesis of l-Vancosamine Derivatives from Methyl α-d-Mannopyranoside
Publication History
Publication Date:
06 February 2006 (online)
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Abstract
Concise synthesis of l-vancosamine, the amino sugar constituent of vancomycin and other antibiotics, has been achieved. The key steps include (1) stereoselective addition of methylcerium reagent to oximino ether, and (2) stereoselective hydrogenation of 5,6-unsaturated glycoside with C(5) inversion to give l-vancosamine derivative. C-Glycosidation of vancosaminyl acetate with iodoresorcinol proceeded in the presence of Sc(OTf)3 in high yield.
Key words
vancosamine - oximino ether - organocerium reagent - stereoselectivity - branched amino sugar - aryl C-glycoside
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References and Notes
Indeed, slightly lower yields were observed when less than five equivalents of the cerium reagent were used under the same conditions.
19Compound 15: mp 168-169 °C (CH2Cl2-hexane); [α]D 28 +10 (c 1.0, CHCl3). 1H NMR (400 MHz, CDCl3): δ = 8.16-8.13 (m, 2 H), 7.67-7.48 (m, 3 H), 6.99 (br s, 1 H), 5.96 (dd, J = 2.7, 10.3 Hz, 1 H), 5.07 (br s, 1 H), 4.17 (dq, J = 1.0, 6.6 Hz, 1 H), 2.61 (dd, J = 2.7, 12.6 Hz, 1 H), 2.15 (s, 3 H), 2.10 (dd, J = 10.3, 12.6 Hz, 1 H), 1.77 (s, 3 H), 1.29 (d, J = 6.6 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 169.1 (C), 167.7 (C), 156.3 (q, J = 37 Hz, C), 134.1 (CH), 130.0 (CH), 128.7 (CH), 128.3 (C), 115.2 (q, J = 290 Hz, C), 90.6 (CH), 73.4 (CH), 69.1 (CH), 57.2 (C), 35.3 (CH2), 21.2 (CH3), 21.0 (CH3), 17.2 (CH3). IR (neat): 3334, 3076, 2989, 1728, 1556, 1452, 1273, 1161, 1049, 908, 758, 715 cm-1. Anal. Calcd: C, 53.60; H, 5.00; N, 3.47. Found: C, 53.39; H, 5.25; N, 3.37.
20Compound 17: mp 89-90 °C (Et2O-hexane); [α]D 29 -0.3 (c 0.98, CHCl3). 1H NMR (400 MHz, CDCl3): δ = 8.38 (s, 1 H), 8.19-8.16 (m, 2 H), 7.68-7.28 (m, 8 H), 7.01 (d, J = 8.5 Hz, 1 H), 6.88 (br s, 1 H), 6.42 (d, J = 8.5 Hz, 1 H), 5.22 (br s, 1 H), 5.16 (s, 2 H), 4.89 (dd, J = 2.7, 12.2 Hz, 1 H), 4.20 (q, J = 6.6 Hz, 1 H), 2.49 (dd, J = 2.7, 12.4 Hz, 1 H), 2.28 (dd, J = 12.2, 12.4 Hz, 1 H), 1.84 (s, 3 H), 1.31 (d, J = 6.6 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 167.6 (C), 158.3 (C), 156.3 (q, J = 37 Hz, C), 155.3 (C), 136.5 (C), 134.1 (CH), 130.1 (CH), 128.9 (CH), 128.5 (CH), 128.2 (C), 127.8 (CH), 127.5 (CH), 126.9 (CH), 118.6 (C), 115.2 (q, J = 290 Hz, C), 104.2 (CH), 79.0 (C), 75.5 (CH), 73.7 (CH), 71.0 (CH), 70.9 (CH2), 56.7 (C), 37.1 (CH2), 20.4 (CH3), 17.8 (CH3). IR (neat): 3340, 3064, 2985, 1728, 1614, 1452, 1269, 1063, 908, 735, 714 cm-1. Anal. Calcd: C, 52.03; H, 4.07; N, 2.09. Found: C, 52.18; H, 4.33; N, 2.14.