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DOI: 10.1055/s-2004-836021
A Convenient Route to Imino Sugars and Analogues of Siastatin B
Publication History
Publication Date:
12 November 2004 (online)
Abstract
A β-lactam template has been used to induce the stereochemistry in a simple route to imino sugars.
Key words
imino sugars - siastatin B - β-Lactam - ring closing metathesis - dihydroxylation
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References
2-( tert -Butyldimethylsilanyloxymethyl)-4,5-dihydroxy-3-hydroxymethylpiperidine-1-carboxylic Acid tert- Butyl Ester ( 15): Osmium tetroxide (0.15 mL, 0.08 M in t-BuOH, 0.0123 mmol) was added to a stirring solution of alkene 4 (0.440 g, 1.23 mmol) and N-methylmorpholine-N-oxide (0.188 g, 1.60 mmol) in acetone (24 mL) and H2O (2.4 mL). The reaction was stirred at 20 °C for 96 h. Sodium metabisulfate (2.33 g, 12.3 mmol) was added and stirred for 1 h. The crude reaction mixture was filtered through celite, the filter cake was washed with EtOAc (2 × 10 mL) and concentrated to a yellow oil. The crude oil was take up in EtOAc (20 mL), washed with 1 M HCl (10 mL) and brine (10 mL), dried with MgSO4 and concentrated. The crude material was purified with flash chromatography to give the desired imino sugar 15 as a white solid: mp 115-116 °C. 1H NMR (500 MHz, 348 K, CDCl3): δ = 0.09 (s, 6 H), 0.91 (s, 9 H), 1.48 (s, 9 H), (ddt, J = 5.7, 5.7, 11.3 Hz, 1 H), 3.13 (br d, J = 14.3 Hz, 1 H), 3.67 (dd, J = 5.0, 10.8 Hz, 1 H), 3.82 (dd, J = 5.6, 10.8 Hz, 1 H), 3.85 (m, 1 H), 3.87 (m, 1 H), 3.92 (dd, J = 5.6, 11.2 Hz, 1 H), 4.05 (br d, J = 10.8 Hz, 1 H), 4.23 (br d, J = 14.3, 1 H), 4.34 (m, 1 H). 13C NMR (500 MHz, 273 K, CDCl3): δ = -5.58, -5.55, 18.05, 18.11, 25.82, 28.37, 28.45, 39.85, 40.20, 44.75, 45.67, 62.33, 62.38, 67.48, 67.72, 69.67, 70.28, 80.32, 80.53, 155.63, 155.84. FTIR (nujol): 3354, 1666, 1455, 1373, 1359, 1310, 1273, 1253, 1172, 1144, 1115, 1092, 1081, 1059, 984, 949, 936, 888 cm-1. MS (EI): m/z (%) = 318 (6), 278 (38), 246 (11), 234 (22), 190 (92), 146 (65), 128 (39), 115 (6), 89 (13), 75 (52), 57 (100), 41 (27), 29 (12). HRMS: m/z [M+] calcd for C18H37NO6SiNa: 414.2288; found: 414.2282.