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Glycosidation, VII. Development of Selective Cytostatica for Cancer Therapy Synthesis of Acetal‐β‐glucosides from Cytotoxic Aldehydes
Author(s) -
Tietze Lutz F.,
Fischer Roland,
Guder HansJ.,
Neumann Manfred
Publication year - 1987
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.198719870839
Subject(s) - acetal , chemistry , trimethylsilyl trifluoromethanesulfonate , trimethylsilyl , aldehyde , ether , organic chemistry , hydrolysis , catalysis
Aldehydes are highly cytotoxic compounds, but they can normally not be used in cancer therapy because of fast binding to serum proteins. However, they could be transformed into acetal‐β‐glucosides 5 , a nontoxic transport form, from which they can be freed by enzymatic or acid‐catalyzed hydrolysis. The acetyl‐protected acetal‐β‐glucosides 4 are obtained in excellent yield and highly selectively by reaction of trimethylsilyl 2,3,4,6‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranoside ( 1c ) and an acetal 2 in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate ( 3 ) in dichloromethane at −70°C. Deacetylation gives the free acetal‐β‐glucosides 5 . Similarly, trimethylsilyl 2,3,4,6‐tetra‐ O ‐benzyl‐β‐glucopyranoside ( 1e ) was used to afford the benzyl‐protected acetal‐β‐glucosides 6 . The formation of 4 or 6 can also be achieved by reaction of 1c or 1e with an aldehyde 8 and an alkyl trimethylsilyl ether 7 in the presence of 3 .