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Glycosidation, 14. Stereoselective synthesis of acetal-β-glucosides by reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose with enol ethers

✍ Scribed by Tietze, Lutz F. ;Lögers, Michael

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
519 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Acetal‐glycosides are a new class of compounds which is of interest in the development of selective anticancer agents. Cytotoxic aldehydes and ketones may be released by enzymatic or acid‐catalyzed hydrolysis preferentially in the tumour tissue. An alternative synthetic route to acetal‐β‐glucosides 4 was developed in connection with these investigations. The acetyl‐protected acetal‐β‐glucosides 3a–h are obtained anomerically pure in 63–95% yield by reaction of 2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranose (1) with an enol ether 2a–h in the presence of catalytic amounts of p‐toluenesulfonic acid in dry tetrahydrofuran at room temperature. Deacetylation with potassium carbonate in methanol gives the free acetal‐β‐glucosides 4a–h.

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