Premium
Glycosidation, 14. Stereoselective synthesis of acetal‐β‐glucosides by reaction of 2,3,4,6‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranose with enol ethers
Author(s) -
Tietze Lutz F.,
Lögers Michael
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900147
Subject(s) - chemistry , acetal , enol , stereoselectivity , potassium carbonate , catalysis , enol ether , hydrolysis , organic chemistry , methanol , glycoside , tetrahydrofuran , yield (engineering) , stereochemistry , solvent , materials science , metallurgy
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 .