Synthesis and glycosidic reaction of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers

Article abstract of DOI:10.1080/07328309608005693

Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular S_N2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.

Full text of DOI:10.1080/07328309608005693

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Journal of Carbohydrate Chemistry
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Synthesis and Glycosidic Reaction of
1,2-Anhydromanno-, Lyxo-, Gluco-, and
Xylofuranose Perbenzyl Ethers
Yuguo Du a & Fanzuo Kong a
a Research Center for Eco-Environmental Sciences Academia Sinica ,
P.O.Box 2871, Beijing, 100085, P.R.China
Published online: 22 Aug 2006.
To cite this article: Yuguo Du & Fanzuo Kong (1996) Synthesis and Glycosidic Reaction of 1,2-
Anhydromanno-, Lyxo-, Gluco-, and Xylofuranose Perbenzyl Ethers, Journal of Carbohydrate
Chemistry, 15:7, 797-817, DOI: 10.1080/07328309608005693
To link to this article: http://dx.doi.org/10.1080/07328309608005693
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