79435-87-3Relevant academic research and scientific papers
Glycosidation, VII. Development of Selective Cytostatica for Cancer Therapy Synthesis of Acetal-β-glucosides from Cytotoxic Aldehydes
Tietze, Lutz F.,Fischer, Roland,Guder, Hans-J.,Neumann, Manfred
, p. 847 - 856 (2007/10/02)
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 deg 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.
