Synthesis of l-Vancosamine Derivatives from Methyl α-d-Mannopyranoside

Day-Shin Hsu; Takashi Matsumoto; Keisuke Suzuki

doi:10.1055/s-2006-926231

LETTER

Synthesis of l-Vancosamine Derivatives from Methyl α-d-Mannopyranoside

Day-Shin Hsu, Takashi Matsumoto, Keisuke Suzuki*
Department of Chemistry, Tokyo Institute of Technology, and SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551, Japan
Fax: +81(3)57342788; e-Mail: ksuzuki@chem.titech.ac.jp;

Abstract

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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

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Compound 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.

Compound 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.