Investigation of the base promoted tandem syn-elimination-Favorskii rearrangement of levoglucosan sulfonates

被引：3

作者：

Muldgaard, L ^{[1
]}

Thomsen, IB ^{[1
]}

Hazell, RG ^{[1
]}

Bols, M ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus, Denmark

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 10期

关键词：

D O I：

10.1039/b200064b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of various 2,3,4-trisulfonated1,6-anhydro-beta-D-glucopyranoses with alkoxide was investigated. Upon treatment with methoxide the tritosylate dagger 5, tris(chlorosulfate) 20 and tris(trifluoromethanesulfonate) 21 all gave 1,5-anhydro-2,3-dideoxy-3-methoxycarbonyl-beta-D-erythro-pentofuranose 6 in 41-57% yield with the yield increasing with improved leaving group ability. The trimesylate double dagger 19 gave the 3,4-epoxide 23 and no rearranged product. Chloroform was found to be the best solvent for obtaining 6, while alcohol as the solvent only gave epoxide 2. A study of different bases showed that the yield of the Favorskii product was increased 10-20% by using ethoxide as base. Reaction of the corresponding chlorosulfonated 1,6-anhydrogalactopyranose or anhydromannopyranose gave the same product though in lower yield. The Favorskii product 6 rearranged in the presence of traces of acid to a 1,5':1',5-dianhydride.

引用

页码：1297 / 1301

页数：5

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