Andreassen Mikkel, Lundt Inge
Department of Chemistry, Technical University of Denmark, Building 201, DK-2800 Kgs. Lyngby, Denmark.
Carbohydr Res. 2006 Jul 24;341(10):1692-6. doi: 10.1016/j.carres.2006.03.037. Epub 2006 Apr 21.
The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-D-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).
天然存在的抗氧化剂阿斯科皮酮P（1,5-脱水-4-脱氧-D-甘油-hex-1-烯-3-酮，1）由稀有糖1,5-脱水-D-果糖（AF，3）经三步反应制备，总产率为36%。因此，3的乙酰化得到烯醇酮3,6-二-O-乙酰基-1,5-脱水-4-脱氧-D-甘油-hex-3-烯-2-吡喃酮（4），其可异构化为2,6-二-O-乙酰基-1,5-脱水-4-脱氧-D-甘油-hex-1-烯-3-酮（6）。在温和条件下6的脱乙酰化得到结晶状的阿斯科皮酮P（1）。
